Heterocylic compound and light-emitting device and electronic apparatus including the heterocyclic compound

ABSTRACT

A light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an interlayer between the first electrode and the second electrode and including an emission layer, wherein the interlayer includes a heterocyclic compound of Formula 1: 
       A 1   B 1 ] n1   Formula 1
 
     wherein, in Formula 1, the variables are defined herein.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority from and the benefit of Korean PatentApplication No. 10-2021-0034236, filed on Mar. 16, 2021, which is herebyincorporated by reference for all purposes as if fully set forth herein.

BACKGROUND Field

Embodiments of the invention relate generally to display devices, andmore particularly, to a heterocyclic compound and to a light-emittingdevice and an electronic apparatus including the heterocyclic compound.

Discussion of the Background

Organic light-emitting devices (OLEDs) are self-emissive devices thathave wide viewing angles, high contrast ratios, short response times,and excellent characteristics in terms of luminance, driving voltage,and response speed, compared to devices in the art.

Organic light-emitting devices may include a first electrode located ona substrate, and a hole transport region, an emission layer, an electrontransport region, and a second electrode sequentially stacked on thefirst electrode. Holes provided from the first electrode may move towardthe emission layer through the hole transport region, and electronsprovided from the second electrode may move toward the emission layerthrough the electron transport region. Carriers, such as holes andelectrons, recombine in the emission layer to produce excitons. Theseexcitons transition from an excited state to a ground state to therebygenerate light.

The above information disclosed in this Background section is only forunderstanding of the background of the inventive concepts, and,therefore, it may contain information that does not constitute priorart.

SUMMARY

When light-emitting devices and electronic apparatuses constructedaccording to the principles and illustrative implementations of theinvention include a heterocyclic compound represented by one or more ofthe formula disclosed herein, the light-emitting devices may have lowdriving voltage, high emission efficiency, and high external quantumefficiency, and high-quality electronic apparatuses may be manufactured.

Additional features of the inventive concepts will be set forth in thedescription which follows, and in part will be apparent from thedescription, or may be learned by practice of the inventive concepts.

According to one aspect of the invention, a light-emitting deviceincludes: a first electrode; a second electrode facing the firstelectrode; and an interlayer between the first electrode and the secondelectrode and including an emission layer, wherein the interlayerincludes a heterocyclic compound of Formula 1:

wherein, in Formulae 1, 1-1, and 1-2, the variables are defined herein.

The heterocyclic compound of Formula 1 may be included in the emissionlayer.

The organometallic compound of Formula 401 may be further included inthe emission layer:

wherein, in Formulae 401 and 402, the variables are defined herein.

The emission layer may be configured to emit blue light.

The emission layer may further include a host, and an amount of the hostmay be greater than an amount of the heterocyclic compound of Formula 1.

The host may include two different host compounds.

The host may include a hole transport host compound and an electrontransport host compound.

The interlayer may further include a hole transport region between thefirst electrode and the emission layer and an electron transport regionbetween the emission layer and the second electrode, the hole transportregion may include a hole injection layer, a hole transport layer, anemission auxiliary layer, an electron blocking layer, or any combinationthereof, and the electron transport region may include a buffer layer, ahole blocking layer, an electron control layer, an electron transportlayer, an electron injection layer, or any combination thereof.

The emission layer may include the heterocyclic compound of Formula 1,the hole transport region may include a compound of Formula 201, acompound of Formula 202, or any combination thereof:

wherein, in Formulae 201 and 202, the variables are defined herein.

Each of Formulae 201 and 202 may include at least one group of FormulaeCY201 to CY217, as defined herein.

The emission layer may include the heterocyclic compound of Formula 1,the electron transport region includes a compound of Formula 601:

[Ar₆₀₁]_(xe11)-[(L₆₀₁)_(xe1)-R₆₀₁]_(xe21)  Formula 601

wherein, in Formula 601, the variables are defined herein.

The electron transport layer in the electron transport region mayinclude a compound of Formula 601, and the electron transport layer mayfurther include a material including a metal.

The material may include a post-transition metal complex, an alkalimetal complex, an alkaline earth metal complex, or any combinationthereof.

The variables Y₁ and Y₂ may each be boron.

The Formula 1-2 may be of Formula 1-2-1 or 1-2-2:

wherein, in Formulae 1-2-1 and 1-2-2, the variables are defined herein.

The Formula 1-2 may be one of Formulae 2-1 to 2-57, the variables aredefined herein.

The Formula 1-1 may be of Formula 1-1-1:

wherein, in Formula 1-1-1, the variables are defined herein.

The light-emitting device may further include a capping layer outsidethe first electrode or the second electrode, and the capping layer mayinclude one or more carbocyclic compounds, heterocyclic compounds,amine-based compounds, porphyrin derivatives, phthalocyaninederivatives, naphthalocyanine derivatives, alkali metal complexes,alkaline earth-based complexes, or any combination thereof.

An electronic apparatus may include the light-emitting device, asdescribed above.

The electronic apparatus may further include a thin-film transistor,wherein the thin-film transistor may include a source electrode and adrain electrode, and the first electrode of the light-emitting devicemay be electrically connected to at least one of the source electrodeand the drain electrode of the thin-film transistor.

It is to be understood that both the foregoing general description andthe following detailed description are illustrative and explanatory andare intended to provide further explanation of the invention as claimed.

BRIEF DESCRIPTION OF THE DRAWINGS

The accompanying drawings, which are included to provide a furtherunderstanding of the invention and are incorporated in and constitute apart of this specification, illustrate illustrative embodiments of theinvention, and together with the description serve to explain theinventive concepts.

FIG. 1 is a schematic cross-sectional view of an embodiment of alight-emitting device constructed according to the principles of theinvention.

FIG. 2 is a schematic cross-sectional view of an embodiment of alight-emitting apparatus including a light-emitting device constructedaccording to the principles of the invention.

FIG. 3 is a schematic cross-sectional view of another embodiment of alight-emitting apparatus including a light-emitting device constructedaccording to the principles of the invention.

DETAILED DESCRIPTION

In the following description, for the purposes of explanation, numerousspecific details are set forth in order to provide a thoroughunderstanding of various embodiments or implementations of theinvention. As used herein “embodiments” and “implementations” areinterchangeable words that are non-limiting examples of devices ormethods employing one or more of the inventive concepts disclosedherein. It is apparent, however, that various embodiments may bepracticed without these specific details or with one or more equivalentarrangements. In other instances, well-known structures and devices areshown in block diagram form in order to avoid unnecessarily obscuringvarious embodiments. Further, various embodiments may be different, butdo not have to be exclusive. For example, specific shapes,configurations, and characteristics of an embodiment may be used orimplemented in another embodiment without departing from the inventiveconcepts.

Unless otherwise specified, the illustrated embodiments are to beunderstood as providing illustrative features of varying detail of someways in which the inventive concepts may be implemented in practice.Therefore, unless otherwise specified, the features, components,modules, layers, films, panels, regions, and/or aspects, etc.(hereinafter individually or collectively referred to as “elements”), ofthe various embodiments may be otherwise combined, separated,interchanged, and/or rearranged without departing from the inventiveconcepts.

The use of cross-hatching and/or shading in the accompanying drawings isgenerally provided to clarify boundaries between adjacent elements. Assuch, neither the presence nor the absence of cross-hatching or shadingconveys or indicates any preference or requirement for particularmaterials, material properties, dimensions, proportions, commonalitiesbetween illustrated elements, and/or any other characteristic,attribute, property, etc., of the elements, unless specified. Further,in the accompanying drawings, the size and relative sizes of elementsmay be exaggerated for clarity and/or descriptive purposes. When anembodiment may be implemented differently, a specific process order maybe performed differently from the described order. For example, twoconsecutively described processes may be performed substantially at thesame time or performed in an order opposite to the described order.Also, like reference numerals denote like elements, and duplicativeexplanations are omitted to avoid redundancy.

When an element, such as a layer, is referred to as being “on,”“connected to,” or “coupled to” another element or layer, it may bedirectly on, connected to, or coupled to the other element or layer orintervening elements or layers may be present. When, however, an elementor layer is referred to as being “directly on,” “directly connected to,”or “directly coupled to” another element or layer, there are nointervening elements or layers present. To this end, the term“connected” may refer to physical, electrical, and/or fluid connection,with or without intervening elements. Further, the D1-axis, the D2-axis,and the D3-axis are not limited to three axes of a rectangularcoordinate system, such as the x, y, and z-axes, and may be interpretedin a broader sense. For example, the D1-axis, the D2-axis, and theD3-axis may be perpendicular to one another, or may represent differentdirections that are not perpendicular to one another. For the purposesof this disclosure, “at least one of X, Y, and Z” and “at least oneselected from the group consisting of X, Y, and Z” may be construed as Xonly, Y only, Z only, or any combination of two or more of X, Y, and Z,such as, for instance, XYZ, XYY, YZ, and ZZ. As used herein, the term“and/or” includes any and all combinations of one or more of theassociated listed items.

Although the terms “first,” “second,” etc. may be used herein todescribe various types of elements, these elements should not be limitedby these terms. These terms are used to distinguish one element fromanother element. Thus, a first element discussed below could be termed asecond element without departing from the teachings of the disclosure.

Spatially relative terms, such as “beneath,” “below,” “under,” “lower,”“above,” “upper,” “over,” “higher,” “side” (e.g., as in “sidewall”), andthe like, may be used herein for descriptive purposes, and, thereby, todescribe one elements relationship to another element(s) as illustratedin the drawings. Spatially relative terms are intended to encompassdifferent orientations of an apparatus in use, operation, and/ormanufacture in addition to the orientation depicted in the drawings. Forexample, if the apparatus in the drawings is turned over, elementsdescribed as “below” or “beneath” other elements or features would thenbe oriented “above” the other elements or features. Thus, the term“below” can encompass both an orientation of above and below.Furthermore, the apparatus may be otherwise oriented (e.g., rotated 90degrees or at other orientations), and, as such, the spatially relativedescriptors used herein interpreted accordingly.

The terminology used herein is for the purpose of describing particularembodiments and is not intended to be limiting. As used herein, thesingular forms, “a,” “an,” and “the” are intended to include the pluralforms as well, unless the context clearly indicates otherwise. Moreover,the terms “comprises,” “comprising,” “includes,” and/or “including,”when used in this specification, specify the presence of statedfeatures, integers, steps, operations, elements, components, and/orgroups thereof, but do not preclude the presence or addition of one ormore other features, integers, steps, operations, elements, components,and/or groups thereof. It is also noted that, as used herein, the terms“substantially,” “about,” and other similar terms, are used as terms ofapproximation and not as terms of degree, and, as such, are utilized toaccount for inherent deviations in measured, calculated, and/or providedvalues that would be recognized by one of ordinary skill in the art.

Various embodiments are described herein with reference to sectionaland/or exploded illustrations that are schematic illustrations ofidealized embodiments and/or intermediate structures. As such,variations from the shapes of the illustrations as a result, forexample, of manufacturing techniques and/or tolerances, are to beexpected. Thus, embodiments disclosed herein should not necessarily beconstrued as limited to the particular illustrated shapes of regions,but are to include deviations in shapes that result from, for instance,manufacturing. In this manner, regions illustrated in the drawings maybe schematic in nature and the shapes of these regions may not reflectactual shapes of regions of a device and, as such, are not necessarilyintended to be limiting.

Unless otherwise defined, all terms (including technical and scientificterms) used herein have the same meaning as commonly understood by oneof ordinary skill in the art to which this disclosure is a part. Terms,such as those defined in commonly used dictionaries, should beinterpreted as having a meaning that is consistent with their meaning inthe context of the relevant art and should not be interpreted in anidealized or overly formal sense, unless expressly so defined herein.

A light-emitting device (for example, an organic light-emitting device)may include a first electrode; a second electrode facing the firstelectrode; an interlayer between the first electrode and the secondelectrode and including the emission layer, and a heterocyclic compoundrepresented by Formula 1.

First, the heterocyclic compound may be represented by Formula 1:

A₁

B₁]_(n1)  Formula 1

wherein, in Formula 1,

A₁ may be a group represented by Formula 1-1,

B₁ may be a group represented by Formula 1-2, and

n1 may be an integer from 1 to 10.

* in Formula 1-2 indicates a binding site to A₁ Formula 1.

Although not wanting to be bound by theory, because the heterocycliccompound represented by Formula 1 includes a group represented byFormula 1-2 as a substituent of Formula 1-1, light-emitting devicesincluding such heterocyclic compounds may have excellent drivingvoltage, emission efficiency, color purity, and lifespancharacteristics. Next, in Formulae 1-1 and 1-2, CY₁ to CY₄ in Formula1-1 may each independently be a C₅-C₃₀ carbocyclic group or a C₁-C₃₀heterocyclic group. For example, CY₁ to CY₄ may each independently be abenzene group, a naphthalene group, an anthracene group, a dibenzofurangroup, a dibenzothiophene group, a carbazole group, a fluorene group, ordibenzosilole group.

In an embodiment, CY₁ and CY₂ may be identical to each other. Forexample, CY₁ and CY₂ may be a benzene group. In one or more embodiments,CY₃ and CY₄ may be identical to each other. For example, CY₃ and CY₄ mayeach be a benzene group. In one or more embodiments, CY₁ to CY₄ may beidentical to each other. For example, CY₁ to CY₄ may each be a benzenegroup. The variables Y₁ and Y₂ in Formula 1-1 may each independently beB, P(═O), or P(═S). In an embodiment, Y₁ and Y₂ may be identical to eachother. For example, Y₁ and Y₂ may each be B.

The variable X₁ in Formula 1-1 may be O, S, Se, Te, N(Ar₁), Al(Ar₁), orP(Ar₁), X₂ may be O, S, Se, Te, N(Ar₂), Al(Ar₂), or P(Ar₂), X₃ may be O,S, Se, Te, N(Ar₃), Al(Ar₃), or P(Ar₃), and X₄ may be O, S, Se, Te,N(Ar₄), Al(Ar₄), or P(Ar₄). In an embodiment, in Formula 1, X₁ may beN(Ar₁), X₂ may be N(Ar₂), X₃ may be N(Ar₃), and X₄ may be N(Ar₄); X₁ maybe N(Ar₁), X₂ may be N(Ar₂), X₃ may be N(Ar₃), and X₄ may be O, S, Se,or Te; X₁ may be N(Ar₁), X₂ may be N(Ar₂), X₃ may be O, S, Se, or Te,and X₄ may be N(Ar₄); X₁ may be N(Ar₁), X₂ may be O, S, Se, or Te, X₃may be N(Ar₃), and X₄ may be N(Ar₄); or X₁ may be O, S, Se, or Te, X₂may be N(Ar₂), X₃ may be N(Ar₃), and X₄ may be N(Ar₄);

The variable X₁ may be N(Ar₁), X₂ may be N(Ar₂), X₃ may be O, S, Se, orTe, X₄ may be O, S, Se, or Te; X₁ may be N(Ar₁), X₂ may be O, S, Se, orTe, X₃ may be N(Ar₃), and X₄ may be O, S, Se, or Te; X₁ may be N(Ar₁),X₂ may be O, S, Se, or Te, X₃ may be O, S, Se, or Te, and X₄ may beN(Ar₄); X₁ may be O, S, Se, or Te, X₂ may be N(Ar₂), X₃ may be N(Ar₃),and X₄ may be O, S, Se, or Te; or X₁ may be O, S, Se, or Te, X₂ may beO, S, Se, or Te, X₃ may be N(Ar₃), and X₄ may be N(Ar₄); X₁ may beN(Ar₁), X₂ may be O, S, Se, or Te, X₃ may be O, S, Se, or Te, and X₄ maybe O, S, Se, or Te; X₁ may be O, S, Se, or Te, X₂ may be N(Ar₂), X₃ maybe O, S, Se, or Te, and X₄ may be O, S, Se, or Te; or X₁ may be O, S,Se, or Te, X₂ may be O, S, Se, or Te, X₃ may be O, S, Se, or Te, and X₄may be N(Ar₄); or X₁ may be O, S, Se, or Te, X₂ may be O, S, Se, or Te,X₃ may be O, S, Se, or Te, and X₄ may be O, S, Se, or Te.

The groups Ar₁ to Ar₁₀ in Formula 1-1 may each independently be abinding site to B₁ in Formula 1, hydrogen, deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, a C₁-C₆ alkyl groupunsubstituted or substituted with at least one R_(10a), a C₂-C₆₀ alkenylgroup unsubstituted or substituted with at least one R_(10a), a C₂-C₆₀alkynyl group unsubstituted or substituted with at least one R_(10a), aC₁-C₆₀ alkoxy group unsubstituted or substituted with at least oneR_(10a), a C₃-C₆₀ carbocyclic group unsubstituted or substituted with atleast one R_(10a), a C₁-C₆₀ heterocyclic group unsubstituted orsubstituted with at least one R_(10a), a C₆-C₆₀ aryloxy groupunsubstituted or substituted with at least one R_(10a), a C₆-C₆₀arylthio group unsubstituted or substituted with at least one R_(10a),—C(Q₁)(Q₂)(Q₃), —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁),—S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂), and at least one of Ar₁ to Ar₁₀ may be abinding site to B₁ in Formula 1.

In an embodiment, Ar₁ to Ar₁₀ may each independently be: a binding siteto B₁ in Formula 1; hydrogen, deuterium, —F, —Cl, —Br, —I, a cyanogroup, a C₁-C₂₀ alkyl group, or a C₁-C₂₀ alkoxy group; a C₁-C₂₀ alkylgroup or a C₁-C₂₀ alkoxy group substituted with deuterium, —CD₃, —CD₂H,—CDH₂, —F, —CF₃, —CF₂H, —CFH₂, —Cl, —CCl₃, —CCl₂H, —CClH₂, —Br, —CBr₃,—CBr₂H, —CBrH₂, —I, —CI₃, —CI₂H, —CIH₂, a cyano group, or anycombination thereof; a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclooctyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a C₁-C₂₀ alkylphenyl group, a naphthyl group,a fluorenyl group, a phenanthrenyl group, an anthracenyl group, athiophenyl group, a furanyl group, an indenyl group, an isoindolylgroup, an indolyl group, a carbazolyl group, a benzofuranyl group, abenzothiophenyl group, a benzosilolyl group, a dibenzofuranyl group, adibenzothiophenyl group, a dibenzosilolyl group, a benzofluorenyl group,a benzocarbazolyl group, a naphthobenzofuranyl group, anaphthobenzothiophenyl group, a naphthobenzosilolyl group, adibenzofluorenyl group, a dibenzocarbazolyl group, a dinaphthofuranylgroup, a dinaphthothiophenyl group, a dinaphthosilolyl group, anindenocarbazolyl group, an indolocarbazolyl group, abenzofuranocarbazolyl group, a benzothienocarbazolyl group, abenzosilolocarbazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolylgroup, an indazolyl group, a purinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a benzoquinoxalinyl group, a quinazolinyl group, abenzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, aphenoxazinyl group, a phenothiazinyl group, a phenoxathinyl group, abenzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, abenzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, abenzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, atetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, atriazinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group,an oxazolopyridinyl group, a thiazolopyridinyl group, abenzonaphthyridinyl group, an azafluorenyl group, anazaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranylgroup, an azadibenzothiophenyl group, an azadibenzosilolyl group, anindenopyrrolyl group, or an indolopyrrolyl group, each unsubstituted orsubstituted with deuterium, —CD₃, —CD₂H, —CDH₂, —F, —CF₃, —CF₂H, —CFH₂,—Cl, —CCl₃, —CCl₂H, —CClH₂, —Br, —CBr₃, —CBr₂H, —CBrH₂, —I, —CI₃, —CI₂H,—CIH₂, a cyano group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctylgroup, an adamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a biphenyl group, a terphenyl group, a C₁-C₂₀ alkylphenylgroup, a naphthyl group, a fluorenyl group, a phenanthrenyl group, ananthracenyl group, a thiophenyl group, a furanyl group, an indenylgroup, an isoindolyl group, an indolyl group, a carbazolyl group, abenzofuranyl group, a benzothiophenyl group, a benzosilolyl group, adibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group,a benzofluorenyl group, a benzocarbazolyl group, a naphthobenzofuranylgroup, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, adibenzofluorenyl group, a dibenzocarbazolyl group, a dinaphthofuranylgroup, a dinaphthothiophenyl group, a dinaphthosilolyl group, anindenocarbazolyl group, an indolocarbazolyl group, abenzofuranocarbazolyl group, a benzothienocarbazolyl group, abenzosilolocarbazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolylgroup, an indazolyl group, a purinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a benzoquinoxalinyl group, a quinazolinyl group, abenzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, aphenoxazinyl group, a phenothiazinyl group, a phenoxathinyl group, abenzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, abenzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, abenzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, atetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, atriazinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group,an oxazolopyridinyl group, a thiazolopyridinyl group, abenzonaphthyridinyl group, an azafluorenyl group, anazaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranylgroup, an azadibenzothiophenyl group, an azadibenzosilolyl group, anindenopyrrolyl group, an indolopyrrolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃),

—N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂),or any combination thereof; or —C(Q₁)(Q₂)(Q₃), —Si(Q₁)(Q₂)(Q₃),—N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁),

—S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂).

For example, Ar₁ to Ar₁₀ may each independently be: a binding site to B₁in Formula 1; a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a biphenyl group, a terphenylgroup, a C₁-C₂₀alkylphenyl group, a naphthyl group, a fluorenyl group, aphenanthrenyl group, an anthracenyl group, a thiophenyl group, a furanylgroup, an indenyl group, an isoindolyl group, an indolyl group, acarbazolyl group, a benzofuranyl group, a benzothiophenyl group, abenzosilolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, adibenzosilolyl group, a benzofluorenyl group, a benzocarbazolyl group, anaphthobenzofuranyl group, a naphthobenzothiophenyl group, anaphthobenzosilolyl group, a dibenzofluorenyl group, a dibenzocarbazolylgroup, a dinaphthofuranyl group, a dinaphthothiophenyl group, adinaphthosilolyl group, an indeno carbazolyl group, an indolocarbazolylgroup, a benzofuranocarbazolyl group, a benzothienocarbazolyl group, ora benzosilolocarbazolyl group, each unsubstituted or substituted withhydrogen, deuterium, —CD₃, —CD₂H, —CDH₂, —F, —CF₃, —CF₂H, —CFH₂, —Cl,—CCl₃, —CCl₂H, —CClH₂, —Br, —CBr₃, —CBr₂H, —CBrH₂, —I, —CI₃, —CI₂H,—CIH₂, a cyano group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctylgroup, an adamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a biphenyl group, a terphenyl group, a C₁-C₂₀ alkylphenylgroup, a naphthyl group, a fluorenyl group, a phenanthrenyl group, ananthracenyl group, a thiophenyl group, a furanyl group, an indenylgroup, an isoindolyl group, an indolyl group, a carbazolyl group, abenzofuranyl group, a benzothiophenyl group, a benzosilolyl group, adibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group,a benzofluorenyl group, a benzocarbazolyl group, a naphthobenzofuranylgroup, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, adibenzofluorenyl group, a dibenzocarbazolyl group, a dinaphthofuranylgroup, a dinaphthothiophenyl group, a dinaphthosilolyl group, anindenocarbazolyl group, an indolocarbazolyl group, abenzofuranocarbazolyl group, a benzothienocarbazolyl group, abenzosilolocarbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂), or anycombination thereof; or —C(Q₁)(Q₂)(Q₃), —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂),—B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂).

In an embodiment, Ar₁₀ may be hydrogen. In an embodiment, when Ar₉indicates a binding site to B₁ in Formula 1, X₂ and X₄ may eachindependently be O, S, Se, or Te. The variable T₁₁ in Formula 1-2 may bea C₃-C₆₀ carbocyclic group unsubstituted or substituted with at leastone R_(10a) or a C₁-C₆₀ heterocyclic group unsubstituted or substitutedwith at least one R_(10a).

In an embodiment, T₁₁ may be i) a group T1, ii) a condensed cyclic groupin which two or more groups T1(s) are condensed with each other, iii) agroup T2, iv) a condensed cyclic group in which two or more groups T2(s)are condensed with each other, or v) a condensed cyclic group in whichone or more groups T2(s) and one or more groups T1(s) are condensed witheach other, each unsubstituted or substituted with at least one R_(10a).

The group T1 may be a cyclopropane group, a cyclobutane group, acyclopentane group, a cyclohexane group, a cycloheptane group, acyclooctane group, a cyclobutene group, a cyclopentene group, acyclopentadiene group, a cyclohexene group, a cyclohexadiene group, acycloheptene group, an adamantane group, a norbornane (or abicyclo[2.2.1]heptane) group, a norbornene group, abicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, abicyclo[2.2.2]octane group, or a benzene group.

The group T2 may be a furan group, a thiophene group, a 1H-pyrrolegroup, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrolegroup, an imidazole group, a pyrazole group, a triazole group, atetrazole group, an oxazole group, an isoxazole group, an oxadiazolegroup, a thiazole group, an isothiazole group, a thiadiazole group, anazasilole group, an azaborole group, a pyridine group, a pyrimidinegroup, a pyrazine group, a pyridazine group, a triazine group, atetrazine group, a pyrrolidine group, an imidazolidine group, adihydropyrrole group, a piperidine group, a tetrahydropyridine group, adihydropyridine group, a hexahydropyrimidine group, atetrahydropyrimidine group, a dihydropyrimidine group, a piperazinegroup, a tetrahydropyrazine group, a dihydropyrazine group, atetrahydropyridazine group, or a dihydropyridazine group.

In Formula 1-2, X₁₁ may be N or C(R₁₁), X₁₂ may be N or C(R₁₂), X₁₃ maybe N or C(R₁₃), and X₁₄ may be N or C(R₁₄). In an embodiment, X₁₁ to X₁₄may be identical to each other. For example, X₁₁ may be C(R₁₁), X₁₂ maybe C(R₁₂), X₁₃ may be C(R₁₃), and X₁₄ may be C(R₁₄).

The variables R₁ to R₄ and R₁₁ to R₁₄ in Formulae 1-1 and 1-2 may eachindependently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, a C₁-C₆₀ alkyl group unsubstitutedor substituted with at least one R_(10a), a C₂-C₆₀ alkenyl groupunsubstituted or substituted with at least one R_(10a), a C₂-C₆₀ alkynylgroup unsubstituted or substituted with at least one R_(10a), a C₁-C₆₀alkoxy group unsubstituted or substituted with at least one R_(10a), aC₃-C₆₀ carbocyclic group unsubstituted or substituted with at least oneR_(10a), a C₁-C₆₀ heterocyclic group unsubstituted or substituted withat least one R_(10a), a C₆-C₆₀ aryloxy group unsubstituted orsubstituted with at least one R_(10a), a C₆-C₆₀ arylthio groupunsubstituted or substituted with at least one R_(10a), —C(Q₁)(Q₂)(Q₃),—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), or—P(═O)(Q₁)(Q₂).

In an embodiment, R₁ to R₄ and R₁₁ to R₁₄ may each independently be:hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a C₁-C₂₀ alkylgroup, or a C₁-C₂₀ alkoxy group; a C₁-C₂₀ alkyl group or a C₁-C₂₀ alkoxygroup substituted with deuterium, —CD₃, —CD₂H, —CDH₂, —F, —CF₃, —CF₂H,—CFH₂, —Cl, —CCl₃, —CCl₂H, —CClH₂, —Br, —CBr₃, —CBr₂H, —CBrH₂, —I, —CI₃,—CI₂H, —CIH₂, a cyano group, or any combination thereof; a cyclopentylgroup, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, anadamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a biphenyl group, a terphenyl group, a C₁-C₂₀ alkylphenylgroup, a naphthyl group, a fluorenyl group, a phenanthrenyl group, ananthracenyl group, a thiophenyl group, a furanyl group, an indenylgroup, an isoindolyl group, an indolyl group, a carbazolyl group, abenzofuranyl group, a benzothiophenyl group, a benzosilolyl group, adibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group,a benzofluorenyl group, a benzocarbazolyl group, a naphthobenzofuranylgroup, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, adibenzofluorenyl group, a dibenzocarbazolyl group, a dinaphthofuranylgroup, a dinaphthothiophenyl group, a dinaphthosilolyl group, anindenocarbazolyl group, an indolocarbazolyl group, abenzofuranocarbazolyl group, a benzothienocarbazolyl group, abenzosilolocarbazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolylgroup, an indazolyl group, a purinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a benzoquinoxalinyl group, a quinazolinyl group, abenzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, aphenoxazinyl group, a phenothiazinyl group, a phenoxathinyl group, abenzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, abenzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, abenzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, atetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, atriazinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group,an oxazolopyridinyl group, a thiazolopyridinyl group, abenzonaphthyridinyl group, an azafluorenyl group, anazaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranylgroup, an azadibenzothiophenyl group, an azadibenzosilolyl group, anindenopyrrolyl group, or an indolopyrrolyl group, each unsubstituted orsubstituted with deuterium, —CD₃, —CD₂H, —CDH₂, —F, —CF₃, —CF₂H, —CFH₂,—Cl, —CCl₃, —CCl₂H, —CClH₂, —Br, —CBr₃, —CBr₂H, —CBrH₂, —I, —CI₃, —CI₂H,—CIH₂, a cyano group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctylgroup, an adamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a biphenyl group, a terphenyl group, a C₁-C₂₀ alkylphenylgroup, a naphthyl group, a fluorenyl group, a phenanthrenyl group, ananthracenyl group, a thiophenyl group, a furanyl group, an indenylgroup, an isoindolyl group, an indolyl group, a carbazolyl group, abenzofuranyl group, a benzothiophenyl group, a benzosilolyl group, adibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group,a benzofluorenyl group, a benzocarbazolyl group, a naphthobenzofuranylgroup, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, adibenzofluorenyl group, a dibenzocarbazolyl group, a dinaphthofuranylgroup, a dinaphthothiophenyl group, a dinaphthosilolyl group, anindenocarbazolyl group, an indolocarbazolyl group, abenzofuranocarbazolyl group, a benzothienocarbazolyl group, abenzosilolocarbazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolylgroup, an indazolyl group, a purinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a benzoquinoxalinyl group, a quinazolinyl group, abenzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, aphenoxazinyl group, a phenothiazinyl group, a phenoxathinyl group, abenzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, abenzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, abenzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, atetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, atriazinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group,an oxazolopyridinyl group, a thiazolopyridinyl group, abenzonaphthyridinyl group, an azafluorenyl group, anazaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranylgroup, an azadibenzothiophenyl group, an azadibenzosilolyl group, anindenopyrrolyl group, an indolopyrrolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃),—N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂),or any combination thereof; or —C(Q₁)(Q₂)(Q₃), —Si(Q₁)(Q₂)(Q₃),—N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂).

The variables a1 and a4 in Formula 1-1 may each independently be aninteger from 0 to 10. The variable a1 indicates the number of R₁(s),when a1 is an integer of 2 or more, two or more R₁(s) may be identicalto or different from each other, a2 indicates the number of R₂(s), whena2 is an integer of 2 or more, two or more R₂(s) may be identical to ordifferent from each other, a3 indicates the number of R₃(s), when a3 isan integer of 2 or more, two or more R₃(s) may be identical to ordifferent from each other, a4 indicates the number of R₄(s), when a4 isan integer of 2 or more, two or more R₄(s) may be identical to ordifferent from each other.

If two or more of a1(s), R₁(s) in Formula 1-1 may optionally be linkedto each other to form a C₃-C₆₀ carbocyclic group unsubstituted orsubstituted with at least one R_(10a) or a C₁-C₆₀ heterocyclic groupunsubstituted or substituted with at least one R_(10a), two or more ofa2 R₂(s) may optionally be linked to each other to form a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_(10a)or a C₁-C₆₀ heterocyclic group unsubstituted or substituted with atleast one R_(10a), two or more of a3 R₃(s) may optionally be linked toeach other to form a C₃-C₆₀ carbocyclic group unsubstituted orsubstituted with at least one R_(10a) or a C₁-C₆₀ heterocyclic groupunsubstituted or substituted with at least one R_(10a), two or more ofa4 R₄(s) may optionally be linked to each other to form a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_(10a)or a C₁-C₆₀ heterocyclic group unsubstituted or substituted with atleast one R_(10a).

Two or more neighboring groups of R₁₁ to R₁₄ in Formula 1-1 mayoptionally be linked to each other to form a C₃-C₆₀ carbocyclic groupunsubstituted or substituted with at least one R_(10a) or a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least oneR_(10a).

Formula 1-1 may be represented by Formula 1-1-1:

wherein, in Formula 1-1-1,

CY₁, CY₂, X₁ to X₄, Y₁, Y₂, Ar₁ to Ar₁₀, R₁, R₂, a1, and a2 are each thesame as described herein,

R_(3a) and R_(3b) are each the same as described in connection with R₃,and

R_(4a) and R_(4b) are each the same as described in connection with R₄.

In an embodiment, a group represented by

in Formula 1-1 may be a group represented by one of Formulae CY1-1 toCY1-10:

wherein, in Formulae CY1-1 to CY1-10,

Y₁₁ may be O, S, Se, Te, N(R_(11a)), C(R_(11a))(R_(11b)), orSi(R_(11a))(R_(11b)),

R_(1a) to R_(1h), R_(11a), and R_(11b) may each be the same as describedin connection with R₁,

* indicates a binding site to X₁ in Formula 1-1, and

*′ indicates a binding site to Y₁ in Formula 1-1.

In an embodiment, a group represented by

in Formula 1-1 may be a group represented by one of Formulae CY2-1 toCY2-10:

wherein, in Formulae CY2-1 to CY2-10,

Y₂₁ may be O, S, Se, Te, N(R_(21a)), C(R_(21a))(R_(21b)), orSi(R_(21a))(R_(21b)),

R_(2a) to R_(2h), R_(21a), and R_(21b) are each the same as described inconnection with R₂,

* indicates a binding site to X₃ in Formula 1-1, and

*′ indicates a binding site to Y₂ in Formula 1-1.

In an embodiment, Formula 1-2 may be represented by Formula 1-2-1 or1-2-2:

wherein, in Formulae 1-2-1 and 1-2-2,

X₁₁ to X₁₄ are each the same as described herein,

X₂₁ may be N or C(R₂₁), X₂₂ may be N or C(R₂₂), X₂₃ may be N or C(R₂₃),X₂₄ may be N or C(R₂₄), and X₂₅ may be N or C(R₂₅),

X₃₁ may be N or C(R₃₁), X₃₂ may be N or C(R₃₂), X₃₃ may be N or C(R₃₃),X₃₄ may be N or C(R₃₄), and X₃₅ may be N or C(R₃₅),

R₂₁ to R₂₅ and R₃₁ to R₃₅ are each the same as described in connectionwith R_(10a),

two or more neighboring groups of R₂₁ to R₂₅ may be optionally linked toeach other to form a C₃-C₆₀ carbocyclic group unsubstituted orsubstituted with at least one R_(10a) or a C₁-C₆₀ heterocyclic groupunsubstituted or substituted with at least one R_(10a), and

two or more neighboring groups of R₃₁ to R₃₅ may be optionally linked toeach other to form a C₃-C₆₀ carbocyclic group unsubstituted orsubstituted with at least one R_(10a) or a C₁-C₆₀ heterocyclic groupunsubstituted or substituted with at least one R_(10a).

For example, Formula 1-2 may be a group selected from Formulae 2-1 to2-57:

wherein, in Formulae 2-1 to 2-57,

V₁ to V₄ may each independently be C or N,

Z₁ to Z₅ may each independently be:

deuterium, —F, —Cl, —Br, —I, a cyano group, a C₁-C₂₀ alkyl group, or aC₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group or a C₁-C₂₀ alkoxy group each substituted withdeuterium, —CD₃, —CD₂H, —CDH₂, —F, —CF₃, —CF₂H, —CFH₂, —Cl, —CCl₃,—CCl₂H, —CClH₂, —Br, —CBr₃, —CBr₂H, —CBrH₂, —I, —CI₃, —CI₂H, —CIH₂, acyano group, or any combination thereof;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclooctyl group, an adamantanyl group, a norbornanyl group, anorbornenyl group, a cyclopentenyl group, a cyclohexenyl group, acycloheptenyl group, a phenyl group, a biphenyl group, a terphenylgroup, a C₁-C₂₀ alkylphenyl group, a naphthyl group, a fluorenyl group,a phenanthrenyl group, an anthracenyl group, a thiophenyl group, afuranyl group, an indenyl group, an isoindolyl group, an indolyl group,a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, abenzosilolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, adibenzosilolyl group, a benzofluorenyl group, a benzocarbazolyl group, anaphthobenzofuranyl group, a naphthobenzothiophenyl group, anaphthobenzosilolyl group, a dibenzofluorenyl group, a dibenzocarbazolylgroup, a dinaphthofuranyl group, a dinaphthothiophenyl group, adinaphthosilolyl group, an indenocarbazolyl group, an indolocarbazolylgroup, a benzofuranocarbazolyl group, a benzothienocarbazolyl group, abenzosilolocarbazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolylgroup, an indazolyl group, a purinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a benzoquinoxalinyl group, a quinazolinyl group, abenzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, aphenoxazinyl group, a phenothiazinyl group, a phenoxathinyl group, abenzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, abenzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, abenzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, atetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, atriazinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group,an oxazolopyridinyl group, a thiazolopyridinyl group, abenzonaphthyridinyl group, an azafluorenyl group, anazaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranylgroup, an azadibenzothiophenyl group, an azadibenzosilolyl group, anindenopyrrolyl group, or an indolopyrrolyl group, each unsubstituted orsubstituted with deuterium, —CD₃, —CD₂H, —CDH₂, —F, —CF₃, —CF₂H, —CFH₂,—Cl, —CCl₃, —CCl₂H, —CClH₂, —Br, —CBr₃, —CBr₂H, —CBrH₂, —I, —CI₃, —CI₂H,—CIH₂, a cyano group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctylgroup, an adamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a biphenyl group, a terphenyl group, a C₁-C₂₀ alkylphenylgroup, a naphthyl group, a fluorenyl group, a phenanthrenyl group, ananthracenyl group, a thiophenyl group, a furanyl group, an indenylgroup, an isoindolyl group, an indolyl group, a carbazolyl group, abenzofuranyl group, a benzothiophenyl group, a benzosilolyl group, adibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group,a benzofluorenyl group, a benzocarbazolyl group, a naphthobenzofuranylgroup, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, adibenzofluorenyl group, a dibenzocarbazolyl group, a dinaphthofuranylgroup, a dinaphthothiophenyl group, a dinaphthosilolyl group, anindenocarbazolyl group, an indolocarbazolyl group, abenzofuranocarbazolyl group, a benzothienocarbazolyl group, abenzosilolocarbazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolylgroup, an indazolyl group, a purinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a benzoquinoxalinyl group, a quinazolinyl group, abenzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, aphenoxazinyl group, a phenothiazinyl group, a phenoxathinyl group, abenzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, abenzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, abenzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, atetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, atriazinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group,an oxazolopyridinyl group, a thiazolopyridinyl group, abenzonaphthyridinyl group, an azafluorenyl group, anazaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranylgroup, an azadibenzothiophenyl group, an azadibenzosilolyl group, anindenopyrrolyl group, an indolopyrrolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃),—N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂),or any combination thereof; or

—C(Q₁)(Q₂)(Q₃), —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁),—S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂),

wherein Q₁ to Q₃ and Q₃₁ to Q₃₃ may each independently be hydrogen;deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitrogroup; a C₁-C₆₀ alkyl group; a C₂-C₆₀ alkenyl group; a C₂-C₆₀ alkynylgroup; a C₁-C₆₀ alkoxy group; or a C₃-C₆₀ carbocyclic group or a C₁-C₆₀heterocyclic group, each unsubstituted or substituted with deuterium,—F, a cyano group, a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkoxy group, a phenylgroup, a biphenyl group, or any combination thereof,

e2 may be an integer from 0 to 2,

e3 may be an integer from 0 to 3,

e4 may be an integer from 0 to 4,

e5 may be an integer from 0 to 5,

e7 may be an integer from 0 to 7,

e11 may be an integer from 0 to 11, and

* indicates a binding site to a neighboring group.

In one embodiment, the heterocyclic compound may be selected fromCompounds 1 to 110:

The heterocyclic compound represented by Formula 1-1 may include atleast one group represented by Formula 1-2 as a substituent in a corestructure represented by Formula 1-1:

Although not wanting to be bound by theory, when the group representedby Formula 1-2 as described above is not included, B atom in afictitious compound having a structure corresponding to Formula 1 may becombined with a nucleophile through an empty P orbital of the B atom sothat a trigonal bond structure of the B atom may be transformed into atetrahedral structure, thereby causing deterioration of an electronicdevice using the fictitious compound. However, the P orbital of the Batom in Formula 1 may be effectively protected through a grouprepresented by Formula 1-2, and thus the trigonal bond structure of theB atom in Formula 1 may be effectively maintained. In addition, althoughthe heterocyclic compound represented by Formula 1 has a multipleresonance planar structure, through a group represented by Formula 1-2,the distance between molecules may increase, causing molecularaggregation and generation of molecular excimer or molecular exciplex,and thereby decreasing the possibility of intermolecular interactionthat may cause reduction in emission efficiency. Moreover, in theheterocyclic compound represented by Formula 1, when an atom in at leastone of X₁₁ to X₁₄ in Formula 1-2 is “N”, for example, because the lonepair electron of the N atom of the pyridine stabilizes the p orbitalwhile showing an electron donating effect, the stability of the boroncompound may be significantly improved. Therefore, the emissionefficiency and/or lifespan of the electronic device including theheterocyclic compound represented by Formula 1, for example, alight-emitting device, may be improved.

The synthesis method of the heterocyclic compound represented by Formula1 may be recognizable by one of ordinary skill in the art by referringto Synthesis Examples and/or Examples provided below.

In some embodiments, the first electrode of the light-emitting devicemay be an anode, the second electrode of the light-emitting device maybe a cathode, the interlayer may further include a hole transport regionlocated between the first electrode and the emission layer and anelectron transport region located between the emission layer and thesecond electrode, the hole transport region may include a hole injectionlayer, a hole transport layer, an emission auxiliary layer, an electronblocking layer, or any combination thereof, and the electron transportregion may include a buffer layer, a hole blocking layer, an electroncontrol layer, an electron transport layer, an electron injection layer,or any combination thereof.

In one or more embodiments, the heterocyclic compound may be includedbetween the first electrode and the second electrode of thelight-emitting device. Accordingly, the heterocyclic compound may beincluded in the interlayer of the light-emitting device, for example, inthe emission layer of the interlayer. The emission layer may emit redlight, green light, blue light, and/or white light. For example, theemission layer may emit blue light. The blue light may have a maximumemission wavelength of, for example, about 400 nm to about 490 nm, orabout 450 nm to about 470 nm. Because the blue light has a maximumemission wavelength of about 450 nm to about 470 nm, manufacturingorganic light-emitting devices having high color purity is possible. Inan embodiment, the emission layer may further include a host, and anamount of the host may be greater than an amount of the heterocycliccompound represented by Formula 1.

In an embodiment, the light-emitting device may include a capping layerlocated outside the first electrode or outside the second electrode. Forexample, the capping layer may include the heterocyclic compoundrepresented by Formula 1. For example, the light-emitting device mayfurther include at least one of a first capping layer located outsidethe first electrode and a second capping layer located outside thesecond electrode, and the heterocyclic compound represented by Formula 1may be included in at least one of the first capping layer and thesecond capping layer. More details for the first capping layer and/orsecond capping layer are the same as described herein. In one or moreembodiments, the light-emitting device may further include: a firstcapping layer located outside the first electrode and including theheterocyclic compound represented by Formula 1; a second capping layerlocated outside the second electrode and including the heterocycliccompound represented by Formula 1; or the first capping layer and thesecond capping layer.

The expression “(an interlayer and/or a capping layer) includes at leastone heterocyclic compound” as used herein may include a case in which“(an interlayer and/or a capping layer) includes identical heterocycliccompounds represented by Formula 1” and a case in which “(an organiclayer) includes two or more different heterocyclic compounds representedby Formula 1”. For example, the interlayer and/or capping layer mayinclude, as the heterocyclic compound, Compound 1 only. In this regard,Compound 1 may be present in the emission layer of the light-emittingdevice. In one or more embodiments, the interlayer may include, as theheterocyclic compound, Compound 1 and Compound 2. In this regard,Compound 1 and Compound 2 may be present in an identical layer (forexample, Compound 1 and Compound 2 may all be present in an emissionlayer), or different layers (for example, Compound 1 may be present inan emission layer and Compound 2 may be present in an electron transportregion).

According to another aspect of the invention an electronic apparatusincluding the light-emitting device may further include a thin-filmtransistor. In one or more embodiments, the electronic apparatus mayfurther include a thin-film transistor including a source electrode anda drain electrode, and the first electrode of the light-emitting devicemay be electrically connected to the source electrode or the drainelectrode. In an embodiment, the electronic apparatus may furtherinclude a color filter, a color conversion layer, a touch screen layer,a polarizing layer, or any combination thereof. More details on theelectronic apparatus are the same as described herein.

According to an embodiment of the invention a heterocyclic compound isrepresented by Formula 1. The detailed description of Formula 1 is thesame as described herein.

Description of FIG. 1

FIG. 1 is a schematic cross-sectional view of an embodiment of alight-emitting device constructed according to the principles of theinvention.

Particularly, FIG. 1 is a schematic cross-sectional view of alight-emitting device 10 according to an embodiment. The light-emittingdevice 10 includes a first electrode 110, an interlayer 130, and asecond electrode 150.

Hereinafter, the structure of the light-emitting device 10 according toan embodiment and an illustrative method of manufacturing thelight-emitting device 10 will be described in connection with FIG. 1.

First Electrode 110

In FIG. 1, a substrate may be additionally located under the firstelectrode 110 or above the second electrode 150. As the substrate, aglass substrate or a plastic substrate may be used. In one or moreembodiments, the substrate may be a flexible substrate, and may includeplastics with excellent heat resistance and durability, such as apolyimide, a polyethylene terephthalate (PET), a polycarbonate, apolyethylene naphthalate, a polyarylate (PAR), a polyetherimide, or anycombination thereof.

The first electrode 110 may be formed by, for example, depositing orsputtering a material for forming the first electrode 110 on thesubstrate. When the first electrode 110 is an anode, a material forforming the first electrode 110 may be a high work function materialthat facilitates injection of holes.

The first electrode 110 may be a reflective electrode, asemi-transmissive electrode, or a transmissive electrode. When the firstelectrode 110 is a transmissive electrode, a material for forming thefirst electrode 110 may include an indium tin oxide (ITO), an indiumzinc oxide (IZO), a tin oxide (SnO₂), a zinc oxide (ZnO), or anycombinations thereof. In one or more embodiments, when the firstelectrode 110 is a semi-transmissive electrode or a reflectiveelectrode, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium(Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver(Mg—Ag), or any combinations thereof may be used as a material forforming a first electrode.

The first electrode 110 may have a single-layered structure consistingof a single layer or a multi-layered structure including a plurality oflayers. For example, the first electrode 110 may have a three-layeredstructure of an ITO/Ag/ITO.

Interlayer 130

The interlayer 130 may be located on the first electrode 110. Theinterlayer 130 may include an emission layer. The interlayer 130 mayfurther include a hole transport region placed between the firstelectrode 110 and the emission layer and an electron transport regionplaced between the emission layer and the second electrode 150.

The interlayer 130 may further include, in addition to various organicmaterials, metal-containing compounds such as organometallic compounds,inorganic materials such as quantum dots, and the like. In one or moreembodiments, the interlayer 130 may include, i) two or more emittingunits sequentially stacked between the first electrode 110 and thesecond electrode 150 and ii) a charge generation layer located betweenthe two or more emitting units. When the interlayer 130 includes anemitting unit and a charge generation layer as described above, thelight-emitting device 10 may be a tandem light-emitting device.

Hole Transport Region in Interlayer 130

The hole transport region may have: i) a single-layered structureconsisting of a single layer consisting of a single material, ii) asingle-layered structure consisting of a single layer consisting of aplurality of different materials, or iii) a multi-layered structureincluding a plurality of layers including different materials. The holetransport region may include a hole injection layer, a hole transportlayer, an emission auxiliary layer, an electron blocking layer, or anycombination thereof.

For example, the hole transport region may have a multi-layeredstructure including a hole injection layer/hole transport layerstructure, a hole injection layer/hole transport layer/emissionauxiliary layer structure, a hole injection layer/emission auxiliarylayer structure, a hole transport layer/emission auxiliary layerstructure, or a hole injection layer/hole transport layer/electronblocking layer structure, wherein, in each structure, layers are stackedsequentially from the first electrode 110.

The hole transport region may include a compound represented by Formula201, a compound represented by Formula 202, or any combination thereof:

wherein, in Formulae 201 and 202,

L₂₀₁ to L₂₀₄ are each independently a C₃-C₆₀ carbocyclic groupunsubstituted or substituted with at least one R_(10a) or a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least oneR_(10a),

L₂₀₅ may be *—O—*′, *—S—*′, *—N(Q₂₀₁)-*′, a C₁-C₂₀ alkylene groupunsubstituted or substituted with at least one R_(10a), a C₂-C₂₀alkenylene group unsubstituted or substituted with at least one R_(10a),a C₃-C₆₀ carbocyclic group unsubstituted or substituted with at leastone R_(10a), or a C₁-C₆₀ heterocyclic group unsubstituted or substitutedwith at least one R_(10a),

xa1 to xa4 are each independently an integer from 0 to 5,

xa5 is an integer from 1 to 10,

R₂₀₁ to R₂₀₄ and Q₂₀₁ are each independently a C₃-C₆₀ carbocyclic groupunsubstituted or substituted with at least one R_(10a) or a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least oneR_(10a),

R₂₀₁ and R₂₀₂ are optionally linked to each other, via a single bond, aC₁-C₅ alkylene group unsubstituted or substituted with at least oneR_(10a), or a C₂-C₅ alkenylene group unsubstituted or substituted withat least one R_(10a), to form a C₈-C₆₀ polycyclic group (for example, acarbazole group or the like) unsubstituted or substituted with at leastone R_(10a) (for example, Compound HT16),

R₂₀₃ and R₂₀₄ are optionally linked to each other, via a single bond, aC₁-C₅ alkylene group unsubstituted or substituted with at least oneR_(10a), or a C₂-C₅ alkenylene group unsubstituted or substituted withat least one R_(10a), to form a C₈-C₆₀ polycyclic group unsubstituted orsubstituted with at least one R_(10a), and

na1 may be an integer from 1 to 4.

In one or more embodiments, each of Formulae 201 and 202 may include atleast one of groups represented by Formulae CY201 to CY217.

The variables R_(10b) and R_(10c) in Formulae CY201 to CY217 are thesame as described in connection with R_(10a), ring CY₂₀₁ to ring CY₂₀₄may each independently be a C₃-C₂₀ carbocyclic group or a C₁-C₂₀heterocyclic group, and at least one hydrogen in Formulae CY201 to CY217may be unsubstituted or substituted with R_(10a).

In an embodiment, ring CY₂₀₁ to ring CY₂₀₄ in Formulae CY201 to CY217may each independently be a benzene group, a naphthalene group, aphenanthrene group, or an anthracene group. In one or more embodiments,each of Formulae 201 and 202 may include at least one of groupsrepresented by Formulae CY201 to CY203.

In one or more embodiments, Formula 201 may include at least one ofgroups represented by Formulae CY201 to CY203 and at least one of groupsrepresented by Formulae CY204 to CY217. In one or more embodiments, xa1in Formula 201 is 1, R₂₀₁ is a group represented by one of FormulaeCY201 to CY203, xa2 may be 0, and R₂₀₂ may be a group represented by oneof Formulae CY204 to CY217. In one or more embodiments, each of Formulae201 and 202 may not include a group represented by one of Formulae CY201to CY203. In one or more embodiments, each of Formulae 201 and 202 maynot include a group represented by one of Formulae CY201 to CY203, andmay include at least one of groups represented by Formulae CY204 toCY217. In one or more embodiments, each of Formulae 201 and 202 may notinclude a group represented by one of Formulae CY201 to CY217.

In an embodiment, the hole transport region may include one of CompoundsHT1 to HT46, 4,4′,4″-tris[phenyl(m-tolyl)amino]triphenylamine(m-MTDATA),1-N,1-N-bis[4-(diphenylamino)phenyl]-4-N,4-N-diphenylbenzene-1,4-diamine(TDATA), 4,4′,4″-tris[2-naphthyl(phenyl)amino]triphenylamine (2-TNATA),bis(naphthalen-1-yl)-N,N′-bis(phenyl)benzidine (NPB or NPD),N4,N4′-di(naphthalen-2-yl)-N4,N4′-diphenyl-[1,1′-biphenyl]-4,4′-diamine(P-NPB), N,N′-bis(3-methylphenyl)-N,N′-diphenylbenzidine (TPD),N,N′-bis(3-methylphenyl)-N,N′-diphenyl-9,9-spirobifluorene-2,7-diamine(Spiro-TPD),N2,N7-di-1-naphthalenyl-N2,N7-diphenyl-9,9′-spirobi[9H-fluorene]-2,7-diamine(Spiro-NPB),N,N′-di(1-naphthyl)-N,N′-diphenyl-2,2′-dimethyl-(1,1′-biphenyl)-4,4′-diamine(methylated NPB),4,4′-cyclohexylidenebis[N,N-bis(4-methylphenyl)benzenamine] (TAPC),N,N,N′,N′-tetrakis(3-methylphenyl)-3,3′-dimethylbenzidine (HMTPD),4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA),polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (PANI/CSA),polyaniline/poly(4-styrenesulfonate) (PANI/PSS),9-(4-tert-Butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole (CzSi) orany combination thereof:

The thickness of the hole transport region may be in a range of about 50Å to about 10,000 Å, for example, about 100 Å to about 4,000 Å. When thehole transport region includes a hole injection layer, a hole transportlayer, or any combination thereof, the thickness of the hole injectionlayer may be in a range of about 100 Å to about 9,000 Å, for example,about 100 Å to about 1,000 Å, and the thickness of the hole transportlayer may be in a range of about 50 Å to about 2,000 Å, for example,about 100 Å to about 1,500 Å. When the thicknesses of the hole transportregion, the hole injection layer and the hole transport layer are withinthese ranges, satisfactory hole transporting characteristics may beobtained without a substantial increase in driving voltage.

The emission auxiliary layer may increase light-emission efficiency bycompensating for an optical resonance distance according to thewavelength of light emitted by an emission layer, and the electronblocking layer may block the leakage of electrons from an emission layerto a hole transport region. Materials that may be included in the holetransport region may be included in the emission auxiliary layer and theelectron blocking layer.

p-Dopant

The hole transport region may further include, in addition to thesematerials, a charge-generation material for the improvement ofconductive properties. The charge-generation material may be uniformlyor non-uniformly dispersed in the hole transport region (for example, inthe form of a single layer consisting of a charge-generation material).The charge-generation material may be, for example, a p-dopant. In oneor more embodiments, the lowest unoccupied molecular orbital (LUMO)energy level of the p-dopant may be about −3.5 eV or less.

In one or more embodiments, the p-dopant may include a quinonederivative, a cyano group-containing compound, a compound containingelement EL1 and element EL2, or any combination thereof. Examples of thequinone derivative are tetracyanoquinodimethane (TCNQ),2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), etc.Examples of the cyano group-containing compound are1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (HAT-CN), and acompound represented by Formula 221 below.

In Formula 221, R₂₂₁ to R₂₂₃ may each independently be a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_(10a)or a C₁-C₆₀ heterocyclic group unsubstituted or substituted with atleast one R_(10a), and one or more of R₂₂₁ to R₂₂₃ may eachindependently be a C₃-C₆₀ carbocyclic group or a C₁-C₆₀ heterocyclicgroup, each substituted with a cyano group; —F; —Cl; —Br; —I; a C₁-C₂₀alkyl group substituted with a cyano group, —F, —Cl, —Br, —I, or anycombination thereof; or any combination thereof. In the compoundcontaining element EL1 and element EL2, element EL1 may be a metal, ametalloid, or any combination thereof, and element EL2 may be anon-metal, a metalloid, or any combination thereof.

Examples of the metal are an alkali metal (for example, lithium (Li),sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); analkaline earth metal (for example, beryllium (Be), magnesium (Mg),calcium (Ca), strontium (Sr), barium (Ba), etc.); a transition metal(for example, titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V),niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten(W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium(Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni),palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au),etc.); a post-transition metal (for example, zinc (Zn), indium (In), tin(Sn), etc.); and a lanthanide metal (for example, lanthanum (La), cerium(Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm),europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium(Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), etc.).

Examples of the metalloid are silicon (Si), antimony (Sb), and tellurium(Te). Examples of the non-metal are oxygen (O) and a halogen (forexample, F, Cl, Br, I, etc.). In one or more embodiments, examples ofthe compound containing element EL1 and element EL2 are a metal oxide, ametal halide (for example, a metal fluoride, a metal chloride, a metalbromide, or a metal iodide), a metalloid halide (for example, ametalloid fluoride, a metalloid chloride, a metalloid bromide, or ametalloid iodide), a metal telluride, or any combination thereof.

Examples of the metal oxide are a tungsten oxide (for example, WO, W₂O₃,WO₂, WO₃, W₂O₅, etc.), a vanadium oxide (for example, VO, V₂O₃, VO₂,V₂O₅, etc.), a molybdenum oxide (MoO, Mo₂O₃, MoO₂, MoO₃, Mo₂O₅, etc.),and a rhenium oxide (for example, ReO₃, etc.). Examples of the metalhalide are an alkali metal halide, an alkaline earth metal halide, atransition metal halide, a post-transition metal halide, and alanthanide metal halide.

Examples of the alkali metal halide are LiF, NaF, KF, RbF, CsF, LiCl,NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI,and CsI. Examples of the alkaline earth metal halide are BeF₂, MgF₂,CaF₂, SrF₂, BaF₂, BeCl₂, MgCl₂, CaCl₂), SrCl₂, BaCl₂, BeBr₂, MgBr₂,CaBr₂, SrBr₂, BaBr₂, BeI₂, MgI₂, CaI₂, SrI₂, and BaI₂.

Examples of the transition metal halide are a titanium halide (forexample, TiF₄, TiCl₄, TiBr₄, TiI₄, etc.), a zirconium halide (forexample, ZrF₄, ZrCl₄, ZrBr₄, ZrI₄, etc.), a hafnium halide (for example,HfF₄, HfCl₄, HfBr₄, HfI₄, etc.), a vanadium halide (for example, VF₃,VCl₃, VBr₃, VI₃, etc.), a niobium halide (for example, NbF₃, NbCl₃,NbBr₃, NbI₃, etc.), a tantalum halide (for example, TaF₃, TaCl₃, TaBr₃,TaI₃, etc.), a chromium halide (for example, CrF₃, CrCl₃, CrBr₃, CrI₃,etc.), a molybdenum halide (for example, MoF₃, MoCl₃, MoBr₃, MoI₃,etc.), a tungsten halide (for example, WF₃, WCl₃, WBr₃, WI₃, etc.), amanganese halide (for example, MnF₂, MnCl₂, MnBr₂, MnI₂, etc.), atechnetium halide (for example, TcF₂, TcCl₂, TcBr₂, TcI₂, etc.), arhenium halide (for example, ReF₂, ReCl₂, ReBr₂, ReI₂, etc.), an ironhalide (for example, FeF₂, FeCl₂, FeBr₂, FeI₂, etc.), a ruthenium halide(for example, RuF₂, RuCl₂, RuBr₂, RuI₂, etc.), an osmium halide (forexample, OsF₂, OsCl₂, OsBr₂, OsI₂, etc.), a cobalt halide (for example,CoF₂, CoCl₂, CoBr₂, CoI₂, etc.), a rhodium halide (for example, RhF₂,RhCl₂, RhBr₂, RhI₂, etc.), an iridium halide (for example, IrF₂, IrCl₂,IrBr₂, IrI₂, etc.), a nickel halide (for example, NiF₂, NiCl₂, NiBr₂,NiI₂, etc.), a palladium halide (for example, PdF₂, PdCl₂, PdBr₂, PdI₂,etc.), a platinum halide (for example, PtF₂, PtCl₂, PtBr₂, PtI₂, etc.),a copper halide (for example, CuF, CuCl, CuBr, CuI, etc.), a silverhalide (for example, AgF, AgCl, AgBr, AgI, etc.), and a gold halide (forexample, AuF, AuCl, AuBr, AuI, etc.).

Examples of the post-transition metal halide are a zinc halide (forexample, ZnF₂, ZnCl₂, ZnBr₂, ZnI₂, etc.), an indium halide (for example,InI₃, etc.), and a tin halide (for example, SnI₂, etc.). Examples of thelanthanide metal halide are YbF, YbF₂, YbF₃, SmF₃, YbCl, YbCl₂, YbCl₃,SmCl₃, YbBr, YbBr₂, YbBr₃, SmBr₃, YbI, YbI₂, YbI₃, and SmI₃. An exampleof the metalloid halide is an antimony halide (for example, SbCl₅,etc.).

Examples of the metal telluride are an alkali metal telluride (forexample, Li₂Te, a na₂Te, K₂Te, Rb₂Te, Cs₂Te, etc.), an alkaline earthmetal telluride (for example, BeTe, MgTe, CaTe, SrTe, BaTe, etc.), atransition metal telluride (for example, TiTe₂, ZrTe₂, HfTe₂, V₂Te₃,Nb₂Te₃, Ta₂Te₃, Cr₂Te₃, Mo₂Te₃, W₂Te₃, MnTe, TcTe, ReTe, FeTe, RuTe,OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu₂Te, CuTe, Ag₂Te, AgTe,Au₂Te, etc.), a post-transition metal telluride (for example, ZnTe,etc.), and a lanthanide metal telluride (for example, LaTe, CeTe, PrTe,NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.).

Emission Layer in Interlayer 130

When the light-emitting device 10 is a full-color light-emitting device,the emission layer may be patterned into a red emission layer, a greenemission layer, and/or a blue emission layer, according to a sub-pixel.In one or more embodiments, the emission layer may have a stackedstructure of two or more layers of a red emission layer, a greenemission layer, and a blue emission layer, in which the two or morelayers contact each other or are separated from each other. In one ormore embodiments, the emission layer may include two or more materialsof a red light-emitting material, a green light-emitting material, and ablue light-emitting material, in which the two or more materials aremixed with each other in a single layer to emit white light. Forexample, the emission layer may emit blue light.

In an embodiment, the emission layer may include the heterocycliccompound represented by Formula 1 as described herein. The emissionlayer may include a host and a dopant. In an embodiment, the dopant mayinclude the heterocyclic compound represented by Formula 1 as describedherein. In this regard, the dopant may include, in addition to theheterocyclic Compound represented by Formula 1, a phosphorescent dopant,a fluorescent dopant, or any combination thereof. The phosphorescentdopant and fluorescent dopant that may be further included in theemission layer in addition to the heterocyclic compound represented byFormula 1 are the same as described below.

The amount of the dopant in the emission layer may be from about 0.01parts by weight to about 15 parts by weight based on 100 parts by weightof the host. In one or more embodiments, the emission layer may includea quantum dot. The emission layer may include a delayed fluorescencematerial. The delayed fluorescence material may act as a host or adopant in the emission layer. The thickness of the emission layer may bein a range of about 100 Å to about 1,000 Å, for example, about 200 Å toabout 600 Å. When the thickness of the emission layer is within theseranges, excellent light-emission characteristics may be obtained withouta substantial increase in driving voltage.

Host

The host may include, for example, a carbazole-containing compound, ananthracene-containing compound, or any combination thereof. In anembodiment, the host may include a compound represented by Formula 301below:

[Ar₃₀₁]_(xb11)-[(L₃₀₁)_(xb1)-R₃₀₁]_(xb21)  Formula 301

wherein, in Formula 301,

Ar₃₀₁ and L₃₀₁ may each independently be a C₃-C₆₀ carbocyclic groupunsubstituted or substituted with at least one R_(10a) or a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least oneR_(10a),

L₃₀₁ may each independently be a divalent C₃-C₆₀ carbocyclic groupunsubstituted or substituted with at least one R_(10a) or a divalentC₁-C₆₀ heterocyclic group unsubstituted or substituted with at least oneR_(10a),

xb11 may be 1, 2, or 3,

xb1 may be an integer from 0 to 5,

R₃₀₁ may be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, a C₁-C₆₀ alkyl group unsubstituted orsubstituted with at least one R_(10a), a C₂-C₆₀ alkenyl groupunsubstituted or substituted with at least one R_(10a), a C₂-C₆₀ alkynylgroup unsubstituted or substituted with at least one R_(10a), a C₁-C₆₀alkoxy group unsubstituted or substituted with at least one R_(10a), aC₃-C₆₀ carbocyclic group unsubstituted or substituted with at least oneR_(10a), a C₁-C₆₀ heterocyclic group unsubstituted or substituted withat least one R_(10a), —Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃), —N(Q₃₀₁)(Q₃₀₂),—B(Q₃₀₁)(Q₃₀₂), —C(═O)(Q₃₀₁), —S(═O)₂(Q₃₀₁), or —P(═O)(Q₃₀₁)(Q₃₀₂),

xb21 may be an integer from 1 to 5, and

wherein R_(10a) is the same as described herein, and Q₃₀₁ to Q₃₀₃ arethe same as described in connection with Q₁.

For example, when xb11 in Formula 301 is 2 or more, two or more ofAr₃₀₁(s) may be linked to each other via a single bond. In one or moreembodiments, the host may include a compound represented by Formula301-1, a compound represented by Formula 301-2, or any combinationthereof:

In Formulae 301-1 and 301-2,

ring A₃₀₁ to ring A₃₀₄ may each independently be a C₃-C₆₀ carbocyclicgroup unsubstituted or substituted with at least one R_(10a) or a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least oneR_(10a), wherein R_(10a) is the same as described herein,

X₃₀₁ may be O, S, N-[(L₃₀₄)_(xb4)-R₃₀₄], C(R₃₀₄)(R₃₀₅), orSi(R₃₀₄)(R₃₀₅),

xb22 and xb23 may each independently be 0, 1, or 2,

L₃₀₁, xb1, and R₃₀₁ are each independently the same as described herein,

L₃₀₂ to L₃₀₄ are each independently the same as described in connectionwith L₃₀₁,

xb2 to xb4 are each independently the same as described in connectionwith xb1, and

R₃₀₂ to R₃₀₅ and R₃₁₁ to R₃₁₄ are each independently the same asdescribed in connection with R₃₀₁.

In one or more embodiments, the host may include an alkali earth metalcomplex, a post-transition metal complex, or any combination thereof. Inone or more embodiments, the host may include a Be complex (for example,Compound H55), an Mg complex, a Zn complex, or any combination thereof.

In an embodiment, the host may include one of Compounds H1 to H124,9,10-di(2-naphthyl)anthracene (ADN),2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN),9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN),4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di(carbazol-9-yl)benzene(mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), or any combinationthereof:

Phosphorescent Dopant

The phosphorescent dopant may include at least one transition metal as acentral metal. The phosphorescent dopant may include a monodentateligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand,a pentadentate ligand, a hexadentate ligand, or any combination thereof.The phosphorescent dopant may be electrically neutral. For example, thephosphorescent dopant may include an organometallic compound representedby Formula 401:

wherein, in Formulae 401 and 402,

M may be transition metal (for example, iridium (Ir), platinum (Pt),palladium (Pd), osmium (Os), titanium (Ti), gold (Au), hafnium (Hf),europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium(Tm)),

L₄₀₁ may be a ligand represented by Formula 402, and xc1 may be 1, 2, or3, wherein when xc1 is two or more, two or more of L₄₀₁(s) may beidentical to or different from each other,

L₄₀₂ may be an organic ligand, and xc2 may be 0, 1, 2, 3, or 4, and whenxc2 is 2 or more, two or more of L₄₀₂(s) may be identical to ordifferent from each other,

X₄₀₁ and X₄₀₂ may each independently be nitrogen or carbon,

ring A₄₀₁ and ring A₄₀₂ may each independently be a C₃-C₆₀ carbocyclicgroup or a C₁-C₆₀ heterocyclic group,

T₄₀₁ may be a single bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—N(Q₄₁₁)-*′,*—C(Q₄₁₁)(Q₄₁₂)-*′, *—C(Q₄₁₁)=C(Q₄₁₂)-*′, *—C(Q₄₁₁)=*′, or *═C═*′,

X₄₀₃ and X₄₀₄ may each independently be a chemical bond (for example, acovalent bond or a coordination bond), O, S, N(Q₄₁₃), B(Q₄₁₃), P(Q₄₁₃),C(Q₄₁₃)(Q₄₁₄), or Si(Q₄₁₃)(Q₄₁₄),

Q₄₁₁ to Q₄₁₄ are each the same as described in connection with Q₁,

R₄₀₁ and R₄₀₂ may each independently be hydrogen, deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀ alkylgroup unsubstituted or substituted with at least one R_(10a), a C₁-C₂₀alkoxy group unsubstituted or substituted with at least one R_(10a), aC₃-C₆₀ carbocyclic group unsubstituted or substituted with at least oneR_(10a), a C₁-C₆₀ heterocyclic group unsubstituted or substituted withat least one R_(10a), —Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃), —N(Q₄₀₁)(Q₄₀₂),—B(Q₄₀₁)(Q₄₀₂), —C(═O)(Q₄₀₁), —S(═O)₂(Q₄₀₁), or —P(═O)(Q₄₀₁)(Q₄₀₂),

Q₄₀₁ to Q₄₀₃ are each the same as described in connection with Q₁,

xc11 and xc12 may each independently be an integer from 0 to 10, and

* and *′ in Formula 402 each indicates a binding site to M in Formula401.

For example, in Formula 402, i) X₄₀₁ may be nitrogen, and X₄₀₂ may becarbon, or ii) each of X₄₀₁ and X₄₀₂ may be nitrogen.

In one or more embodiments, when xc1 in Formula 402 is 2 or more, tworing A₄₀₁(s) in two or more of L₄₀₁(s) may be optionally linked to eachother via T₄₀₂, which is a linking group, and two ring A₄₀₂(s) areoptionally linked to each other via T₄₀₃, which is a linking group (seeCompounds PD1 to PD4 and PD7). The groups T₄₀₂ and T₄₀₃ are each thesame as described in connection with T₄₀₁.

The group L₄₀₂ in Formula 401 may be an organic ligand. For example,L₄₀₂ may include a halogen group, a diketone group (for example, anacetylacetonate group), a carboxylic acid group (for example, apicolinate group), a —C(═O) group, an isonitrile group, a —CN group, aphosphorus group (for example, a phosphine group, a phosphite group,etc.), or any combination thereof.

The phosphorescent dopant may include, for example, one of compounds PD1to PD39, or any combination thereof:

Fluorescent Dopant

The fluorescent dopant may include an amine group-containing compound, astyryl group-containing compound, or any combination thereof. In one ormore embodiments, the fluorescent dopant may include a compoundrepresented by Formula 501:

wherein, in Formula 501,

Ar₅₀₁, L₅₀₁ to L₅₀₃, R₅₀₁, and R₅₀₂ may each independently be a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_(10a)or a C₁-C₆₀ heterocyclic group unsubstituted or substituted with atleast one R_(10a),

L₅₀₁ to L₅₀₃ may each independently be a divalent C₃-C₆₀ carbocyclicgroup unsubstituted or substituted with at least one R_(10a) or adivalent C₁-C₆₀ heterocyclic group unsubstituted or substituted with atleast one R_(10a), wherein R_(10a) is the same as described herein,

xd1 to xd3 may each independently be 0, 1, 2, or 3, and

xd4 may be 1, 2, 3, 4, 5, or 6.

In one or more embodiments, Ar₅₀₁ in Formula 501 may be a condensedcyclic group (for example, an anthracene group, a chrysene group, or apyrene group) in which three or more monocyclic groups are condensedtogether.

In one or more embodiments, xd4 in Formula 501 may be 2.

In one or more embodiments, the fluorescent dopant may include: one ofCompounds FD1 to FD36; DPVBi; DPAVBi; or any combination thereof:

Electron Transport Region in Interlayer 130

The electron transport region may have: i) a single-layered structureconsisting of a single layer consisting of a single material, ii) asingle-layered structure consisting of a single layer consisting of aplurality of different materials, or iii) a multi-layered structureincluding a plurality of layers including different materials. Theelectron transport region may include a buffer layer, a hole blockinglayer, an electron control layer, an electron transport layer, anelectron injection layer, or any combination thereof.

In an embodiment, the electron transport region may have an electrontransport layer/electron injection layer structure, a hole blockinglayer/electron transport layer/electron injection layer structure, anelectron control layer/electron transport layer/electron injection layerstructure, or a buffer layer/electron transport layer/electron injectionlayer structure, wherein, for each structure, constituting layers aresequentially stacked from an emission layer.

In an embodiment, the electron transport region (for example, the bufferlayer, the hole blocking layer, the electron control layer, or theelectron transport layer in the electron transport region) may include ametal-free compound including at least one π electron-deficientnitrogen-containing C₁-C₆₀ cyclic group.

In an embodiment, the electron transport region may include a compoundrepresented by Formula 601 below:

[Ar₆₀₁]_(xe11)-[(L₆₀₁)_(xe1)-R₆₀₁]_(xe21)  Formula 601

wherein, in Formula 601,

Ar₆₀₁ and L₆₀₁ may each independently be a C₃-C₆₀ carbocyclic groupunsubstituted or substituted with at least one R_(10a) or a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least oneR_(10a),

L₆₀₁ may each independently be a divalent C₃-C₆₀ carbocyclic groupunsubstituted or substituted with at least one R_(10a) or a divalentC₁-C₆₀ heterocyclic group unsubstituted or substituted with at least oneR_(10a), wherein R_(10a) is the same as described herein,

xe11 may be 1, 2, or 3,

xe1 may be 0, 1, 2, 3, 4, or 5,

R₆₀₁ may be a C₃-C₆₀ carbocyclic group unsubstituted or substituted withat least one R_(10a), a C₁-C₆₀ heterocyclic group unsubstituted orsubstituted with at least one R_(10a), —Si(Q₆₀₁)(Q₆₀₂)(Q₆₀₃),—C(═O)(Q₆₀₁), —S(═O)₂(Q₆₀₁), or —P(═O)(Q₆₀₁)(Q₆₀₂),

Q₆₀₁ to Q₆₀₃ are the same as described in connection with Q₁,

xe21 may be 1, 2, 3, 4, or 5, and

one or more of Ar₆₀₁, L₆₀₁, and R₆₀₁ may each independently be a πelectron-deficient nitrogen-containing C₁-C₆₀ cyclic group unsubstitutedor substituted with at least one R_(10a).

For example, when xe11 in Formula 601 is 2 or more, two or more ofAr₆₀₁(s) may be linked via a single bond. In one or more embodiments,Ar₆₀₁ in Formula 601 may be a substituted or unsubstituted anthracenegroup. In an embodiment, the electron transport region may include acompound represented by Formula 601-1:

wherein, in Formula 601-1,

X₆₁₄ may be N or C(R₆₁₄), X₆₁₅ may be N or C(R₆₁₅), X₆₁₆ may be N orC(R₆₁₆), one or more of X₆₁₄ to X₆₁₆ may be N,

L₆₁₁ to L₆₁₃ are the same as described in connection with L₆₀₁,

xe611 to xe613 are the same as described in connection with xe1,

R₆₁₁ to R₆₁₃ are the same as described in connection with R₆₀₁, and

R₆₁₄ to R₆₁₆ may each independently be hydrogen, deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a C₃-C₆₀ carbocyclic group unsubstitutedor substituted with at least one R_(10a), or a C₁-C₆₀ heterocyclic groupunsubstituted or substituted with at least one R_(10a). For example, xe1and xe611 to xe613 in Formulae 601 and 601-1 may each independently be0, 1, or 2.

The electron transport region may include one of Compounds ET1 to ET45,2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP),4,7-diphenyl-1,10-phenanthroline (Bphen),tris-(8-hydroxyquinoline)aluminum (Alq₃),bis(2-methyl-8-quinolinolato-N1,O8)-(1,1′-biphenyl-4-olato)aluminum(BAlq),3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole(TAZ), 4-(naphthalen-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ),Diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide (TSPO1),1,3,5-Tris(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBI), or anycombination thereof:

The thickness of the electron transport region may be from about 100 Åto about 5,000 Å, for example, from about 160 Å to about 4,000 Å. Whenthe electron transport region includes the buffer layer, the holeblocking layer, the electron control layer, the electron transportlayer, or any combination thereof, the thickness of the buffer layer,the hole blocking layer, or the electron control layer may eachindependently be from about 20 Å to about 1,000 Å, for example, about 30Å to about 300 Å, and the thickness of the electron transport layer maybe from about 100 Å to about 1,000 Å, for example, about 150 Å to about500 Å. When the thicknesses of the buffer layer, hole blocking layer,electron control layer, electron transport layer and/or electrontransport layer are within these ranges, satisfactory electrontransporting characteristics may be obtained without a substantialincrease in driving voltage.

The electron transport region (for example, the electron transport layerin the electron transport region) may further include, in addition tothe materials described above, a metal-containing material. Themetal-containing material may include an alkali metal complex, analkaline earth metal complex, or any combination thereof. The metal ionof an alkali metal complex may be a Li ion, a Na ion, a K ion, a Rb ion,or a Cs ion, and the metal ion of the alkaline earth metal complex maybe a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. A ligandcoordinated with the metal ion of the alkali metal complex or thealkaline earth-metal complex may include a hydroxyquinoline, ahydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, ahydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole,a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, ahydroxyphenylpyridine, a hydroxyphenylbenzimidazole, ahydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, acyclopentadiene, or any combination thereof.

For example, the metal-containing material may include a Li complex. TheLi complex may include, for example, Compound ET-D1 (lithium quinolate,LiQ) or ET-D2:

The electron transport region may include an electron injection layerthat facilitates the injection of electrons from the second electrode150. The electron injection layer may directly contact the secondelectrode 150.

The electron injection layer may have: i) a single-layered structureconsisting of a single layer consisting of a single material, ii) asingle-layered structure consisting of a single layer consisting of aplurality of different materials, or iii) a multi-layered structureincluding a plurality of layers including different materials.

The electron injection layer may include an alkali metal, an alkalineearth metal, a rare earth metal, an alkali metal-containing compound, analkaline earth metal-containing compound, a rare earth metal-containingcompound, an alkali metal complex, an alkaline earth metal complex, arare earth metal complex, or any combination thereof. The alkali metalmay include Li, Na, K, Rb, Cs, or any combination thereof. The alkalineearth metal may include Mg, Ca, Sr, Ba, or any combination thereof. Therare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combinationthereof.

The alkali metal-containing compound, the alkaline earthmetal-containing compound, and the rare earth metal-containing compoundmay be oxides, halides (for example, fluorides, chlorides, bromides, oriodides), or tellurides of the alkali metal, the alkaline earth metal,and the rare earth metal, or any combination thereof.

The alkali metal-containing compound may include alkali metal oxides,such as Li₂O, Cs₂O, or K₂O, alkali metal halides, such as LiF, NaF, CsF,KF, LiI, NaI, CsI, or KI, or any combination thereof. The alkaline earthmetal-containing compound may include an alkaline earth metal compound,such as BaO, SrO, CaO, Ba_(x)Sr_(1-x)O (x is a real number satisfyingthe condition of 0<x<1), Ba_(x)Ca_(1-x)O (x is a real number satisfyingthe condition of 0<x<1), or the like. The rare earth metal-containingcompound may include YbF₃, ScF₃, Sc₂O₃, Y₂O₃, Ce₂O₃, GdF₃, TbF₃, YbI₃,ScI₃, TbI₃, or any combination thereof. In one or more embodiments, therare earth metal-containing compound may include a lanthanide metaltelluride. Examples of the lanthanide metal telluride are LaTe, CeTe,PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe,LuTe, La₂Te₃, Ce₂Te₃, Pr₂Te₃, Nd₂Te₃, Pm₂Te₃, Sm₂Te₃, Eu₂Te₃, Gd₂Te₃,Tb₂Te₃, Dy₂Te₃, Ho₂Te₃, Er₂Te₃, Tm₂Te₃, Yb₂Te₃, and Lu₂Te₃.

The alkali metal complex, the alkaline earth-metal complex, and the rareearth metal complex may include i) one of ions of the alkali metal, thealkaline earth metal, and the rare earth metal and ii), as a ligandlinked to the metal ion, for example, a hydroxyquinoline, ahydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, ahydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole,a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, ahydroxyphenylpyridine, a hydroxyphenyl benzimidazole, ahydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, acyclopentadiene, or any combination thereof.

The electron injection layer may consist of an alkali metal, an alkalineearth metal, a rare earth metal, an alkali metal-containing compound, analkaline earth metal-containing compound, a rare earth metal-containingcompound, an alkali metal complex, an alkaline earth metal complex, arare earth metal complex, or any combination thereof, as describedabove. In one or more embodiments, the electron injection layer mayfurther include an organic material (for example, a compound representedby Formula 601).

In one or more embodiments, the electron injection layer may consist ofi) an alkali metal-containing compound (for example, an alkali metalhalide), ii) a) an alkali metal-containing compound (for example, analkali metal halide); and b) an alkali metal, an alkaline earth metal, arare earth metal, or any combination thereof. In one or moreembodiments, the electron injection layer may be a KI:Yb co-depositedlayer, an RbI:Yb co-deposited layer, or the like.

When the electron injection layer further includes an organic material,an alkali metal, an alkaline earth metal, a rare earth metal, an alkalimetal-containing compound, an alkaline earth metal-containing compound,a rare earth metal-containing compound, an alkali metal complex, analkaline earth-metal complex, a rare earth metal complex, or anycombination thereof may be homogeneously or non-homogeneously dispersedin a matrix including the organic material.

The thickness of the electron injection layer may be in a range of about1 Å to about 100 Å, and, for example, about 3 Å to about 90 Å. When thethickness of the electron injection layer is within the range describedabove, the electron injection layer may have satisfactory electroninjection characteristics without a substantial increase in drivingvoltage.

Second Electrode 150

The second electrode 150 may be located on the interlayer 130 havingsuch a structure. The second electrode 150 may be a cathode, which is anelectron injection electrode, and as the material for the secondelectrode 150, a metal, an alloy, an electrically conductive compound,or any combination thereof, each having a low work function, may beused.

In one or more embodiments, the second electrode 150 may include lithium(Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium(Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver(Mg—Ag), ytterbium (Yb), silver-ytterbium (Ag—Yb), an ITO, an IZO, orany combination thereof. The second electrode 150 may be a transmissiveelectrode, a semi-transmissive electrode, or a reflective electrode. Thesecond electrode 150 may have a single-layered structure or amulti-layered structure including two or more layers.

Capping Layer

A first capping layer may be located outside the first electrode 110,and/or a second capping layer may be located outside the secondelectrode 150. In detail, the light-emitting device 10 may have astructure in which the first capping layer, the first electrode 110, theinterlayer 130, and the second electrode 150 are sequentially stacked inthis stated order, a structure in which the first electrode 110, theinterlayer 130, the second electrode 150, and the second capping layerare sequentially stacked in this stated order, or a structure in whichthe first capping layer, the first electrode 110, the interlayer 130,the second electrode 150, and the second capping layer are sequentiallystacked in this stated order.

Light generated in an emission layer of the interlayer 130 of thelight-emitting device 10 may be extracted toward the outside through thefirst electrode 110, which is a semi-transmissive electrode or atransmissive electrode, and the first capping layer or light generatedin an emission layer of the interlayer 130 of the light-emitting device10 may be extracted toward the outside through the second electrode 150,which is a semi-transmissive electrode or a transmissive electrode, andthe second capping layer.

Although not wanting to be bound by theory, the first capping layer andthe second capping layer may increase external emission efficiencyaccording to the principle of constructive interference. Accordingly,the light extraction efficiency of the light-emitting device 10 isincreased, so that the emission efficiency of the light-emitting device10 may be improved. Each of the first capping layer and second cappinglayer may include a material having a refractive index (at 589 nm) ofabout 1.6 or more.

The first capping layer and the second capping layer may eachindependently be an organic capping layer including an organic material,an inorganic capping layer including an inorganic material, or anorganic-inorganic composite capping layer including an organic materialand an inorganic material.

At least one selected from the first capping layer and the secondcapping layer may each independently include carbocyclic compounds,heterocyclic compounds, amine group-containing compounds, porphyrinderivatives, phthalocyanine derivatives, naphthalocyanine derivatives,alkali metal complexes, alkaline earth metal complexes, or anycombination thereof. The carbocyclic compound, the heterocycliccompound, and the amine group-containing compound may be optionallysubstituted with a substituent containing O, N, S, Se, Si, F, Cl, Br, I,or any combination thereof. In one or more embodiments, at least one ofthe first capping layer and the second capping layer may eachindependently include an amine group-containing compound.

In one or more embodiments, at least one of the first capping layer andthe second capping layer may each independently include a compoundrepresented by Formula 201, a compound represented by Formula 202, orany combination thereof.

In one or more embodiments, at least one of the first capping layer andthe second capping layer may each independently include one of CompoundsHT28 to HT33, one of Compounds CP1 to CP6,N4,N4′-di(naphthalen-2-yl)-N4,N4′-diphenyl-[1,1′-biphenyl]-4,4′-diamine(β-NPB), or any combination thereof:

Electronic Apparatus

The light-emitting device 10 may be included in various electronicapparatuses. In one or more embodiments, the electronic apparatusincluding the light-emitting device may be a light-emitting apparatus,an authentication apparatus, or the like.

The electronic apparatus (for example, light-emitting apparatus) mayfurther include, in addition to the light-emitting device 10, i) a colorfilter, ii) a color conversion layer, or iii) a color filter and a colorconversion layer. The color filter and/or the color conversion layer maybe located in at least one traveling direction of light emitted from thelight-emitting device 10. In one or more embodiments, the light emittedfrom the light-emitting device 10 may be blue light or white light. Thelight-emitting device 10 may be the same as described above. In one ormore embodiments, the color conversion layer may include quantum dots.The quantum dot may be, for example, a quantum dot as described herein.

The electronic apparatus may include a first substrate. The firstsubstrate may include a plurality of subpixel areas, the color filtermay include a plurality of color filter areas respectively correspondingto the subpixel areas, and the color conversion layer may include aplurality of color conversion areas respectively corresponding to thesubpixel areas.

A pixel-defining film may be located among the subpixel areas to defineeach of the subpixel areas. The color filter may further include aplurality of color filter areas and light-shielding patterns locatedamong the color filter areas, and the color conversion layer may includea plurality of color conversion areas and light-shielding patternslocated among the color conversion areas.

The color filter areas (or the color conversion areas) may include afirst area emitting first color light, a second area emitting secondcolor light, and/or a third area emitting third color light, and thefirst color light, the second color light, and/or the third color lightmay have different maximum emission wavelengths from one another. In oneor more embodiments, the first color light may be red light, the secondcolor light may be green light, and the third color light may be bluelight. In one or more embodiments, the color filter areas (or the colorconversion areas) may include quantum dots. In detail, the first areamay include a red quantum dot, the second area may include a greenquantum dot, and the third area may not include a quantum dot. Thequantum dot is the same as described herein. The first area, the secondarea, and/or the third area may each include a scatterer.

In one or more embodiments, the light-emitting device 10 may emit afirst light, the first area may absorb the first light to emit firstfirst-color light, the second area may absorb the first light to emitsecond first-color light, and the third area may absorb the first lightto emit third first-color light. In this regard, the first first-colorlight, the second first-color light, and the third first-color light mayhave different maximum emission wavelengths. In detail, the first lightmay be blue light, the first first-color light may be red light, thesecond first-color light may be green light, and the third first-colorlight may be blue light.

The electronic apparatus may further include a thin-film transistor inaddition to the light-emitting device 10 as described above. Thethin-film transistor may include a source electrode, a drain electrode,and an activation layer, wherein any one of the source electrode and thedrain electrode may be electrically connected to any one of the firstelectrode and the second electrode of the light-emitting device 10.

The thin-film transistor may further include a gate electrode, a gateinsulating film, and the like. The activation layer may include acrystalline silicon, an amorphous silicon, an organic semiconductor, anoxide semiconductor, and the like.

The electronic apparatus may further include a sealing portion forsealing the light-emitting device 10. The sealing portion and/or thecolor conversion layer may be placed between the color filter and thelight-emitting device 10. The sealing portion allows light from thelight-emitting device 10 to be extracted to the outside, whilesimultaneously preventing ambient air and moisture from penetrating intothe light-emitting device 10. The sealing portion may be a sealingsubstrate including a transparent glass substrate or a plasticsubstrate. The sealing portion may be a thin-film encapsulation layerincluding at least one layer of an organic layer and/or an inorganiclayer. When the sealing portion is a thin film encapsulation layer, theelectronic apparatus may be flexible.

Various functional layers may be additionally located on the sealingportion, in addition to the color filter and/or the color conversionlayer, according to the use of the electronic apparatus. The functionallayers may include a touch screen layer, a polarizing layer, and thelike. The touch screen layer may be a pressure-sensitive touch screenlayer, a capacitive touch screen layer, or an infrared touch screenlayer. The authentication apparatus may be, for example, a biometricauthentication apparatus that authenticates an individual by usingbiometric information of a living body (for example, fingertips, pupils,etc.). The authentication apparatus may further include, in addition tothe light-emitting device 10, a biometric information collector.

The electronic apparatus may take the form of or be applied to variousdisplays, light sources, lighting, personal computers (for example, amobile personal computer), mobile phones, digital cameras, electronicorganizers, electronic dictionaries, electronic game machines, medicalinstruments (for example, electronic thermometers, sphygmomanometers,blood glucose meters, pulse measurement devices, pulse wave measurementdevices, electrocardiogram displays, ultrasonic diagnostic devices, orendoscope displays), fish finders, various measuring instruments, meters(for example, meters for a vehicle, an aircraft, and a vessel),projectors, and the like.

Description of FIGS. 2 and 3

FIG. 2 is a schematic cross-sectional view of an embodiment of alight-emitting apparatus including a light-emitting device constructedaccording to the principles of the invention.

The light-emitting apparatus 180 of FIG. 2 includes a substrate 100, athin-film transistor (TFT) 200, a light-emitting device 10, and anencapsulation portion 300 that seals the light-emitting device 10.

The substrate 100 may be a flexible substrate, a glass substrate, or ametal substrate. A buffer layer 210 may be formed on the substrate 100.The buffer layer 210 may prevent penetration of impurities through thesubstrate 100 and may provide a substantially flat surface on thesubstrate 100.

The TFT 200 may be located on the buffer layer 210. The TFT 200 mayinclude an activation layer 220, a gate electrode 240, a sourceelectrode 260, and a drain electrode 270.

The activation layer 220 may include an inorganic semiconductor such assilicon or a polysilicon, an organic semiconductor, or an oxidesemiconductor, and may include a source region, a drain region and achannel region.

A gate insulating film 230 for insulating the activation layer 220 fromthe gate electrode 240 may be located on the activation layer 220, andthe gate electrode 240 may be located on the gate insulating film 230.An interlayer insulating film 250 is located on the gate electrode 240.The interlayer insulating film 250 may be placed between the gateelectrode 240 and the source electrode 260 to insulate the gateelectrode 240 from the source electrode 260 and between the gateelectrode 240 and the drain electrode 270 to insulate the gate electrode240 from the drain electrode 270.

The source electrode 260 and the drain electrode 270 may be located onthe interlayer insulating film 250. The interlayer insulating film 250and the gate insulating film 230 may be formed to expose the sourceregion and the drain region of the activation layer 220, and the sourceelectrode 260 and the drain electrode 270 may be in contact with theexposed portions of the source region and the drain region of theactivation layer 220.

The TFT 200 is electrically connected to a light-emitting device 10 todrive the light-emitting device 10, and is covered by a passivationlayer 280. The passivation layer 280 may include an inorganic insulatingfilm, an organic insulating film, or any combination thereof. Thelight-emitting device 10 is provided on the passivation layer 280. Thelight-emitting device 10 may include a first electrode 110, aninterlayer 130, and a second electrode 150.

The first electrode 110 may be formed on the passivation layer 280. Thepassivation layer 280 does not completely cover the drain electrode 270and exposes a portion of the drain electrode 270, and the firstelectrode 110 is connected to the exposed portion of the drain electrode270.

A pixel defining layer 290 containing an insulating material may belocated on the first electrode 110. The pixel defining layer 290 exposesa region of the first electrode 110, and an interlayer 130 may be formedin the exposed region of the first electrode 110. The pixel defininglayer 290 may be a polyimide or a polyacrylic organic film. At leastsome layers of the interlayer 130 may extend beyond the upper portion ofthe pixel defining layer 290 to be located in the form of a commonlayer.

The second electrode 150 may be located on the interlayer 130, and acapping layer 170 may be additionally formed on the second electrode150. The capping layer 170 may be formed to cover the second electrode150.

The encapsulation portion 300 may be located on the capping layer 170.The encapsulation portion 300 may be located on a light-emitting device10 to protect the light-emitting device from moisture or oxygen. Theencapsulation portion 300 may include: an inorganic film including asilicon nitride (SiN_(x)), a silicon oxide (SiO_(x)), an indium tinoxide, an indium zinc oxide, or any combination thereof; an organic filmincluding a polyethylene terephthalate, a polyethylene naphthalate, apolycarbonate, a polyimide, a polyethylene sulfonate, apolyoxymethylene, a polyarylate, a hexamethyldisiloxane, an acrylicresin (for example, a polymethyl methacrylate, a polyacrylic acid, orthe like), an epoxy-based resin (for example, an aliphatic glycidylether (AGE), or the like), or any combination thereof; or anycombination of the inorganic film and the organic film.

FIG. 3 is a schematic cross-sectional view of another embodiment of alight-emitting apparatus including a light-emitting device constructedaccording to the principles of the invention.

The light-emitting apparatus 190 of FIG. 3 is the same as thelight-emitting apparatus 180 of FIG. 2, except that a light-shieldingpattern 500 and a functional region 400 are additionally located on theencapsulation portion 300. The functional region 400 may be acombination of i) a color filter area, ii) a color conversion area, oriii) a combination of the color filter area and the color conversionarea. In one or more embodiments, the light-emitting device 10 includedin the light-emitting apparatus 190 of FIG. 3 may be a tandemlight-emitting device.

Manufacturing Method

Respective layers included in the hole transport region, the emissionlayer, and respective layers included in the electron transport regionmay be formed in a certain region by using one or more suitable methodsselected from vacuum deposition, spin coating, casting,Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, andlaser-induced thermal imaging.

When layers constituting the hole transport region, an emission layer,and layers constituting the electron transport region are formed byvacuum deposition, the deposition may be performed at a depositiontemperature of about 100° C. to about 500° C., a vacuum degree of about10⁻⁸ torr to about 10⁻³ torr, and a deposition speed of about 0.01 Å/secto about 100 Å/sec, depending on a material to be included in a layer tobe formed and the structure of a layer to be formed.

Definition of Terms

As used herein, “interlayer” as used herein refers to a single layerand/or all layers between a first electrode and a second electrode of alight-emitting device. The wording “an (interlayer and/or capping layer)includes fused cyclic compound” may be interpreted as a case in which“an (interlayer and/or capping layer) includes at least one identicalfused cyclic compound represented by Formula 1 or an (interlayer and/orcapping layer) includes two or more different fused cyclic compoundsrepresented by Formula 1.”

As used herein, the term “energy level” may be expressed in “electronvolts” and abbreviated as “eV”.

As used herein, the term “atom” may mean an element or its correspondingradical bonded to one or more other atoms.

The terms “hydrogen” and “deuterium” refer to their respective atoms andcorresponding radicals with the deuterium radical abbreviated “-D”, andthe terms “—F, —Cl, —Br, and —I” are radicals of, respectively,fluorine, chlorine, bromine, and iodine.

As used herein, a substituent for a monovalent group, e.g., alkyl, mayalso be, independently, a substituent for a corresponding divalentgroup, e.g., alkylene.

The term “C₃-C₆₀ carbocyclic group” as used herein refers to a cyclicgroup consisting of carbon only as a ring-forming atom and having threeto sixty carbon atoms, and the term “C₁-C₆₀ heterocyclic group” as usedherein refers to a cyclic group that has one to sixty carbon atoms andfurther has, in addition to carbon, a heteroatom as a ring-forming atom.The C₃-C₆₀ carbocyclic group and the C₁-C₆₀ heterocyclic group may eachbe a monocyclic group consisting of one ring or a polycyclic group inwhich two or more rings are fused with each other. For example, theC₁-C₆₀ heterocyclic group has 3 to 61 ring-forming atoms.

The “cyclic group” as used herein may include the C₃-C₆₀ carbocyclicgroup, and the C₁-C₆₀ heterocyclic group.

The term “π electron-rich C₃-C₆₀ cyclic group” as used herein refers toa cyclic group that has three to sixty carbon atoms and does not include*—N═*′ as a ring-forming moiety, and the term “π electron-deficientnitrogen-containing C₁-C₆₀ cyclic group” as used herein refers to aheterocyclic group that has one to sixty carbon atoms and includes*—N═*′ as a ring-forming moiety.

For example, the C₃-C₆₀ carbocyclic group may be i) a group T1G or ii) afused cyclic group in which two or more groups T1G are fused with eachother, for example, a cyclopentadiene group, an adamantane group, anorbornane group, a benzene group, a pentalene group, a naphthalenegroup, an azulene group, an indacene group, an acenaphthylene group, aphenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a perylene group, a pentaphene group, a heptalene group, anaphthacene group, a picene group, a hexacene group, a pentacene group,a rubicene group, a coronene group, an ovalene group, an indene group, afluorene group, a spirobifluorene group, a benzofluorene group, anindenophenanthrene group, or an indenoanthracene group.

The C₁-C₆₀ heterocyclic group may be i) a group T2G, ii) a fused cyclicgroup in which two or more groups T2G are fused with each other, or iii)a fused cyclic group in which at least one group T2G and at least onegroup T1G are fused with each other, for example, a pyrrole group, athiophene group, a furan group, an indole group, a benzoindole group, anaphthoindole group, an isoindole group, a benzoisoindole group, anaphthoisoindole group, a benzosilole group, a benzothiophene group, abenzofuran group, a carbazole group, a dibenzosilole group, adibenzothiophene group, a dibenzofuran group, an indenocarbazole group,an indolocarbazole group, a benzofurocarbazole group, abenzothienocarbazole group, a benzosilolocarbazole group, abenzoindolocarbazole group, a benzocarbazole group, a benzonaphthofurangroup, a benzonaphthothiophene group, a benzonaphthosilole group, abenzofurodibenzofuran group, a benzofurodibenzothiophene group, abenzothienodibenzothiophene group, a pyrazole group, an imidazole group,a triazole group, an oxazole group, an isoxazole group, an oxadiazolegroup, a thiazole group, an isothiazole group, a thiadiazole group, abenzopyrazole group, a benzimidazole group, a benzoxazole group, abenzoisoxazole group, a benzothiazole group, a benzoisothiazole group, apyridine group, a pyrimidine group, a pyrazine group, a pyridazinegroup, a triazine group, a quinoline group, an isoquinoline group, abenzoquinoline group, a benzoisoquinoline group, a quinoxaline group, abenzoquinoxaline group, a quinazoline group, a benzoquinazoline group, aphenanthroline group, a cinnoline group, a phthalazine group, anaphthyridine group, an imidazopyridine group, an imidazopyrimidinegroup, an imidazotriazine group, an imidazopyrazine group, animidazopyridazine group, an azacarbazole group, an azafluorene group, anazadibenzosilole group, an azadibenzothiophene group, an azadibenzofurangroup, etc.

The π electron-rich C₃-C₆₀ cyclic group may be i) a group T1G, ii) afused cyclic group in which two or more groups T1G are fused with eachother, iii) a group T3G, iv) a fused cyclic group in which two or moregroups T3G are fused with each other, or v) a fused cyclic group inwhich at least one group T3G and at least one group T1G are fused witheach other, for example, the C₃-C₆₀ carbocyclic group, a 1H-pyrrolegroup, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrolegroup, a thiophene group, a furan group, an indole group, a benzoindolegroup, a naphthoindole group, an isoindole group, a benzoisoindolegroup, a naphthoisoindole group, a benzosilole group, a benzothiophenegroup, a benzofuran group, a carbazole group, a dibenzosilole group, adibenzothiophene group, a dibenzofuran group, an indenocarbazole group,an indolocarbazole group, a benzofurocarbazole group, abenzothienocarbazole group, a benzosilolocarbazole group, abenzoindolocarbazole group, a benzocarbazole group, a benzonaphthofurangroup, a benzonaphthothiophene group, a benzonaphthosilole group, abenzofurodibenzofuran group, a benzofurodibenzothiophene group, abenzothienodibenzothiophene group, etc.

The π electron-deficient nitrogen-containing C₁-C₆₀ cyclic group may bei) a group T4G, ii) a fused cyclic group in which two or more groups T4Gare fused with each other, iii) a fused cyclic group in which at leastone group T4G and at least one group T1G are fused with each other, iv)a fused cyclic group in which at least one group T4G and at least onegroup T3G are fused with each other, or v) a fused cyclic group in whichat least one group T4G, at least one group T1G, and at least one groupT3G are fused with one another, for example, a pyrazole group, animidazole group, a triazole group, an oxazole group, an isoxazole group,an oxadiazole group, a thiazole group, an isothiazole group, athiadiazole group, a benzopyrazole group, a benzimidazole group, abenzoxazole group, a benzoisoxazole group, a benzothiazole group, abenzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazinegroup, a pyridazine group, a triazine group, a quinoline group, anisoquinoline group, a benzoquinoline group, a benzoisoquinoline group, aquinoxaline group, a benzoquinoxaline group, a quinazoline group, abenzoquinazoline group, a phenanthroline group, a cinnoline group, aphthalazine group, a naphthyridine group, an imidazopyridine group, animidazopyrimidine group, an imidazotriazine group, an imidazopyrazinegroup, an imidazopyridazine group, an azacarbazole group, an azafluorenegroup, an azadibenzosilole group, an azadibenzothiophene group, anazadibenzofuran group, etc.

The group T1G may be a cyclopropane group, a cyclobutane group, acyclopentane group, a cyclohexane group, a cycloheptane group, acyclooctane group, a cyclobutene group, a cyclopentene group, acyclopentadiene group, a cyclohexene group, a cyclohexadiene group, acycloheptene group, an adamantane group, a norbornane (or abicyclo[2.2.1]heptane) group, a norbornene group, abicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, abicyclo[2.2.2]octane group, or a benzene group.

The group T2G may be a furan group, a thiophene group, a 1H-pyrrolegroup, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrolegroup, an imidazole group, a pyrazole group, a triazole group, atetrazole group, an oxazole group, an isoxazole group, an oxadiazolegroup, a thiazole group, an isothiazole group, a thiadiazole group, anazasilole group, an azaborole group, a pyridine group, a pyrimidinegroup, a pyrazine group, a pyridazine group, a triazine group, atetrazine group, a pyrrolidine group, an imidazolidine group, adihydropyrrole group, a piperidine group, a tetrahydropyridine group, adihydropyridine group, a hexahydropyrimidine group, atetrahydropyrimidine group, a dihydropyrimidine group, a piperazinegroup, a tetrahydropyrazine group, a dihydropyrazine group, atetrahydropyridazine group, or a dihydropyridazine group.

The group T3G may be a furan group, a thiophene group, a 1H-pyrrolegroup, a silole group, or a borole group.

The group T4G may be a 2H-pyrrole group, a 3H-pyrrole group, animidazole group, a pyrazole group, a triazole group, a tetrazole group,an oxazole group, an isoxazole group, an oxadiazole group, a thiazolegroup, an isothiazole group, a thiadiazole group, an azasilole group, anazaborole group, a pyridine group, a pyrimidine group, a pyrazine group,a pyridazine group, a triazine group, or a tetrazine group.

The terms “the cyclic group, the C₃-C₆₀ carbocyclic group, the C₁-C₆₀heterocyclic group, the π electron-rich C₃-C₆₀ cyclic group, or the πelectron-deficient nitrogen-containing C₁-C₆₀ cyclic group” as usedherein refer to a group fused to any cyclic group or a polyvalent group(for example, a divalent group, a trivalent group, a tetravalent group,etc.), depending on the structure of a formula in connection with whichthe terms are used. In an embodiment, “a benzene group” may be a benzogroup, a phenyl group, a phenylene group, or the like, which may beeasily understand by one of ordinary skill in the art according to thestructure of a formula including the “benzene group.”

Examples of the monovalent C₃-C₆₀ carbocyclic group and the monovalentC₁-C₆₀ heterocyclic group are a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic fused polycyclic group, and amonovalent non-aromatic fused heteropolycyclic group, and examples ofthe divalent C₃-C₆₀ carbocyclic group and the monovalent C₁-C₆₀heterocyclic group are a C₃-C₁₀ cycloalkylene group, a C₁-C₁₀heterocycloalkylene group, a C₃-C₁₀ cycloalkenylene group, a C₁-C₁₀heterocycloalkenylene group, a C₆-C₆₀ arylene group, a C₁-C₆₀heteroarylene group, a divalent non-aromatic fused polycyclic group, anda substituted or unsubstituted divalent non-aromatic fusedheteropolycyclic group.

The term “C₁-C₆₀ alkyl group” as used herein refers to a linear orbranched aliphatic hydrocarbon monovalent group that has one to sixtycarbon atoms, and examples thereof are a methyl group, an ethyl group,an n-propyl group, an isopropyl group, an n-butyl group, a sec-butylgroup, an isobutyl group, a tert-butyl group, an n-pentyl group, atert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentylgroup, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, anisohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptylgroup, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, ann-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group,an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonylgroup, an n-decyl group, an isodecyl group, a sec-decyl group, and atert-decyl group. The term “C₁-C₆₀ alkylene group” as used herein refersto a divalent group having a structure corresponding to the C₁-C₆₀ alkylgroup.

The term “C₂-C₆₀ alkenyl group” as used herein refers to a monovalenthydrocarbon group having at least one carbon-carbon double bond in themiddle or at the terminus of the C₂-C₆₀ alkyl group, and examplesthereof are an ethenyl group, a propenyl group, and a butenyl group. Theterm “C₂-C₆₀ alkenylene group” as used herein refers to a divalent grouphaving a structure corresponding to the C₂-C₆₀ alkenyl group.

The term “C₂-C₆₀ alkynyl group” as used herein refers to a monovalenthydrocarbon group having at least one carbon-carbon triple bond in themiddle or at the terminus of the C₂-C₆₀ alkyl group, and examplesthereof include an ethynyl group and a propynyl group. The term “C₂-C₆₀alkynylene group” as used herein refers to a divalent group having astructure corresponding to the C₂-C₆₀ alkynyl group.

The term “C₁-C₆₀ alkoxy group” as used herein refers to a monovalentgroup represented by —OA₁₀₁ (wherein A₁₀₁ is the C₁-C₆₀ alkyl group),and examples thereof include a methoxy group, an ethoxy group, and anisopropyloxy group.

The term “C₃-C₁₀ cycloalkyl group” as used herein refers to a monovalentsaturated hydrocarbon cyclic group having 3 to 10 carbon atoms, andexamples thereof are a cyclopropyl group, a cyclobutyl group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctylgroup, an adamantanyl group, a norbornanyl group (orbicyclo[2.2.1]heptyl group), a bicyclo[1.1.1]pentyl group, abicyclo[2.1.1]hexyl group, and a bicyclo[2.2.2]octyl group. The term“C₃-C₁₀ cycloalkylene group” as used herein refers to a divalent grouphaving a structure corresponding to the C₃-C₁₀ cycloalkyl group.

The term “C₁-C₁₀ heterocycloalkyl group” as used herein refers to amonovalent cyclic group that further includes, in addition to a carbonatom, at least one heteroatom as a ring-forming atom and has 1 to 10carbon atoms, and examples thereof are a 1,2,3,4-oxatriazolidinyl group,a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term“C₁-C₁₀ heterocycloalkylene group” as used herein refers to a divalentgroup having a structure corresponding to the C₁-C₁₀ heterocycloalkylgroup.

The term C₃-C₁₀ cycloalkenyl group used herein refers to a monovalentcyclic group that has three to ten carbon atoms and at least onecarbon-carbon double bond in the ring thereof and no aromaticity, andexamples thereof are a cyclopentenyl group, a cyclohexenyl group, and acycloheptenyl group. The term “C₃-C₁₀ cycloalkenylene group” as usedherein refers to a divalent group having a structure corresponding tothe C₃-C₁₀ cycloalkenyl group.

The term “C₁-C₁₀ heterocycloalkenyl group” as used herein refers to amonovalent cyclic group that has, in addition to a carbon atom, at leastone heteroatom as a ring-forming atom, 1 to 10 carbon atoms, and atleast one carbon-carbon double bond in the cyclic structure thereof.Examples of the C₁-C₁₀ heterocycloalkenyl group include a4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, anda 2,3-dihydrothiophenyl group. The term “C₁-C₁₀ heterocycloalkenylenegroup” as used herein refers to a divalent group having a structurecorresponding to the C₁-C₁₀ heterocycloalkenyl group.

The term “C₆-C₆₀ aryl group” as used herein refers to a monovalent grouphaving a carbocyclic aromatic system having six to sixty carbon atoms,and the term “C₆-C₆₀ arylene group” as used herein refers to a divalentgroup having a carbocyclic aromatic system having six to sixty carbonatoms. Examples of the C₆-C₆₀ aryl group are a phenyl group, apentalenyl group, a naphthyl group, an azulenyl group, an indacenylgroup, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenylgroup, a heptalenyl group, a naphthacenyl group, a picenyl group, ahexacenyl group, a pentacenyl group, a rubicenyl group, a coronenylgroup, and an ovalenyl group. When the C₆-C₆₀ aryl group and the C₆-C₆₀arylene group each include two or more rings, the rings may be fusedwith each other.

The term “C₁-C₆₀ heteroaryl group” as used herein refers to a monovalentgroup having a heterocyclic aromatic system that has, in addition to acarbon atom, at least one heteroatom as a ring-forming atom, and 1 to 60carbon atoms. The term “C₁-C₆₀ heteroarylene group” as used hereinrefers to a divalent group having a heterocyclic aromatic system thathas, in addition to a carbon atom, at least one heteroatom as aring-forming atom, and 1 to 60 carbon atoms. Examples of the C₁-C₆₀heteroaryl group are a pyridinyl group, a pyrimidinyl group, a pyrazinylgroup, a pyridazinyl group, a triazinyl group, a quinolinyl group, abenzoquinolinyl group, an isoquinolinyl group, a benzoisoquinolinylgroup, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinylgroup, a benzoquinazolinyl group, a cinnolinyl group, a phenanthrolinylgroup, a phthalazinyl group, and a naphthyridinyl group. When the C₁-C₆₀heteroaryl group and the C₁-C₆₀ heteroarylene group each include two ormore rings, the rings may be fused with each other.

The term “monovalent non-aromatic fused polycyclic group” as used hereinrefers to a monovalent group (for example, having 8 to 60 carbon atoms)having two or more rings fused to each other, only carbon atoms asring-forming atoms, and no aromaticity in its entire molecularstructure. Examples of the monovalent non-aromatic fused polycyclicgroup are an indenyl group, a fluorenyl group, a spiro-bifluorenylgroup, a benzofluorenyl group, an indenophenanthrenyl group, and anindeno anthracenyl group. The term “divalent non-aromatic fusedpolycyclic group” as used herein refers to a divalent group having astructure corresponding to a monovalent non-aromatic fused polycyclicgroup.

The term “monovalent non-aromatic fused heteropolycyclic group” as usedherein refers to a monovalent group (for example, having 1 to 60 carbonatoms) having two or more rings fused to each other, at least oneheteroatom other than carbon atoms, as a ring-forming atom, andnon-aromaticity in its entire molecular structure. Examples of themonovalent non-aromatic fused heteropolycyclic group are a pyrrolylgroup, a thiophenyl group, a furanyl group, an indolyl group, abenzoindolyl group, a naphtho indolyl group, an isoindolyl group, abenzoisoindolyl group, a naphthoisoindolyl group, a benzosilolyl group,a benzothiophenyl group, a benzofuranyl group, a carbazolyl group, adibenzosilolyl group, a dibenzothiophenyl group, a dibenzofuranyl group,an azacarbazolyl group, an azafluorenyl group, an azadibenzosilolylgroup, an azadibenzothiophenyl group, an azadibenzofuranyl group, apyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolylgroup, an oxazolyl group, an isoxazolyl group, a thiazolyl group, anisothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, abenzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, abenzothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolylgroup, an imidazopyridinyl group, an imidazopyrimidinyl group, animidazotriazinyl group, an imidazopyrazinyl group, an imidazopyridazinylgroup, an indenocarbazolyl group, an indolocarbazolyl group, abenzofurocarbazolyl group, a benzothienocarbazolyl group, abenzosilolocarbazolyl group, a benzoindolocarbazolyl group, abenzocarbazolyl group, a benzonaphthofuranyl group, abenzonaphthothiophenyl group, a benzonaphthosilolyl group, abenzofurodibenzofuranyl group, a benzofurodibenzothiophenyl group, and abenzothienodibenzothiophenyl group. The term “divalent non-aromaticfused heteropolycyclic group” as used herein refers to a divalent grouphaving a structure corresponding to a monovalent non-aromatic fusedheteropolycyclic group.

The term “C₆-C₆₀ aryloxy group” as used herein indicates —OA₁₀₂ (whereinA₁₀₂ is the C₆-C₆₀ aryl group), and the term “C₆-C₆₀ arylthio group” asused herein indicates —SA₁₀₃ (wherein A₁₀₃ is the C₆-C₆₀ aryl group).

The term “C₇-C₆₀ aryl alkyl group” used herein refers to -A₁₀₄A₁₀₅(where A₁₀₄ may be a C₁-C₅₄ alkylene group, and A₁₀₅ may be a C₆-C₅₉aryl group), and the term C₂-C₆₀ heteroaryl alkyl group” used hereinrefers to -A₁₀₆A₁₀₇ (where A₁₀₆ may be a C₁-C₅₉ alkylene group, and A₁₀₇may be a C₁-C₅₉ heteroaryl group).

The term “R_(10a)” as used herein refers to:

deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or anitro group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, ora C₁-C₆₀ alkoxy group, each unsubstituted or substituted with deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, aC₃-C₆₀ carbocyclic group, a C₁-C₆₀ heterocyclic group, a C₆-C₆₀ aryloxygroup, a C₆-C₆₀ arylthio group, a C₇-C₆₀ aryl alkyl group, a C₂-C₆₀heteroaryl alkyl group, —Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂),—C(═O)(Q₁₁), —S(═O)₂(Q₁₁), —P(═O)(Q₁₁)(Q₁₂), or any combination thereof;

a C₃-C₆₀ carbocyclic group, a C₁-C₆₀ heterocyclic group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₇-C₆₀ aryl alkyl group, or aC₂-C₆₀ heteroaryl alkyl group, each unsubstituted or substituted withdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynylgroup, a C₁-C₆₀ alkoxy group, a C₃-C₆₀ carbocyclic group, a C₁-C₆₀heterocyclic group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₇-C₆₀ aryl alkyl group, a C₂-C₆₀ heteroaryl alkyl group,—Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁),—S(═O)₂(Q₂₁), —P(═O)(Q₂₁)(Q₂₂), or any combination thereof; or

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), or —P(═O)(Q₃₁)(Q₃₂),

The groups Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃ and Q₃₁ to Q₃₃ used hereinmay each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; ahydroxyl group; a cyano group; a nitro group; a C₁-C₆₀ alkyl group; aC₂-C₆₀ alkenyl group; a C₂-C₆₀ alkynyl group; a C₁-C₆₀ alkoxy group; aC₃-C₆₀ carbocyclic group or a C₁-C₆₀ heterocyclic group, eachunsubstituted or substituted with deuterium, —F, a cyano group, a C₁-C₆₀alkyl group, a C₁-C₆₀ alkoxy group, a phenyl group, a biphenyl group, orany combination thereof; a C₇-C₆₀ aryl alkyl group; or a C₂-C₆₀heteroaryl alkyl group.

The term “heteroatom” as used herein refers to any atom other than acarbon atom. Examples of the heteroatom are O, S, N, P, Si, B, Ge, Se,and any combination thereof.

The term “the third-row transition metal” used herein includes hafnium(Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium(Ir), platinum (Pt), gold (Au), etc.

As used herein, the term “Ph” refers to a phenyl group, the term “Me”refers to a methyl group, the term “Et” refers to an ethyl group, theterm “tert-Bu” or “Bu^(t)” refers to a tert-butyl group, and the term“OMe” refers to a methoxy group.

The term “biphenyl group” as used herein refers to “a phenyl groupsubstituted with a phenyl group.” In other words, the “biphenyl group”is a substituted phenyl group having a C₆-C₆₀ aryl group as asubstituent.

The term “terphenyl group” as used herein refers to “a phenyl groupsubstituted with a biphenyl group”. In other words, the “terphenylgroup” is a substituted phenyl group having, as a substituent, a C₆-C₆₀aryl group substituted with a C₆-C₆₀ aryl group.

The abbreviation “eq.” means “mole equivalent”.

The symbols * and *′ as used herein, unless defined otherwise, eachrefer to a binding site to a neighboring atom in a corresponding formulaor moiety.

An expression “B is used instead of A” means that the identical molarequivalent of B was used in place of A in the same molar equivalent.

EXAMPLES Synthesis Example 1: Synthesis of Compound 1

Synthesis of Intermediate Compound 1-a

In an argon atmosphere,5-chloro-N1,N1,N3,N3-tetraphenylbenzene-1,3-diamine (50 gram (g), 112millimole (mmol)), 2-(pyridine-2-yl)aniline (19 g, 112 mmol), sodiumtert-butoxide (32 g, 336 mmol), tris-tert-butyl phosphine (5 ml, 11.2mmol), and tris(dibenzylideneacetone)dipalladium (0) Pd₂dba₃ (5.12 g,5.6 mmol) were added to a 2 liter (L) flask and dissolved in 1 L ofo-xylene, and the reaction solution was stirred at temperature of 140°C. for 12 hours. After cooling, water (1 L) and ethylacetate (300 ml)were added thereto for extraction and collection of an organic layer,and was dried using magnesium sulfate (MgSO₄) and filtered. The filteredsolution was placed under reduced pressure to remove solvent therefrom,and the obtained solid was purified and separated by columnchromatography using silica gel and using dichloromethane (CH₂Cl₂) andhexane as development solvents to thereby obtain Intermediate compound1-a (white solid, 41 g, 64%). The obtained white solid was identified byESI-LCMS as Intermediate compound 1-a.

ESI-LCMS: [M]⁺: C₄₁H₃₂N₄. 580.2612.

Synthesis of Intermediate Compound 1-b

In an argon atmosphere, Compound 1-a (40 g, 69 mmol),3-bromo-iodobenzene (19.5 g, 69 mmol), sodium tert-butoxide (20 g, 207mmol), 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (BINAP in an amountof 4.3 g in 7.0 mmol), and Pd₂dba₃ (3.1 g, 3.5 mmol) were added to a 2 Lflask and dissolved in 700 milliliter (ml) of toluene, and the reactionsolution was stirred at a temperature of 100° C. for 12 hours. Aftercooling, water (1 L) and ethylacetate (300 ml) were added thereto forextraction and collection of an organic layer, and was dried using MgSO₄and filtered. The filtered solution was placed under reduced pressure toremove solvent therefrom, and the obtained solid was purified andseparated by column chromatography using silica gel using CH₂Cl₂ andhexane as development solvents to thereby obtain Intermediate compound1-b (white solid, 36 g, 72%). The obtained white solid was identified byESI-LCMS as Intermediate compound 1-b.

ESI-LCMS: [M]⁺: C₄₇H₃₅N₄Br. 734.2020.

Synthesis of Intermediate Compound 1-c

In an argon atmosphere,5-chloro-N1,N1,N3,N3-tetraphenylbenzene-1,3-diamine (50 g, 112 mmol),aniline (10.7 g, 112 mmol), sodium tert-butoxide (32 g, 336 mmol),tris-tert-butyl phosphine (5 ml, 11.2 mmol), and Pd₂dba₃ (3.1 g, 3.5mmol) were added to a 2 L flask and dissolved in 1 L of o-xylene, andthe reaction solution was stirred at temperature of 140° C. for 12hours. After cooling, water (1 L) and ethylacetate (300 ml) were addedthereto for extraction and collection of an organic layer, and was driedusing MgSO₄ and filtered. The filtered solution was placed under reducedpressure to remove solvent therefrom, and the obtained solid waspurified and separated by column chromatography using silica gel usingCH₂Cl₂ and hexane as development solvents to thereby obtain Intermediatecompound 1-c (white solid, 38 g, 68 wt. %). The obtained white solid wasidentified by ESI-LCMS as Intermediate compound 1-c.

ESI-LCMS: [M]⁺: C₃₆H₂₉N₃. 503.2412.

Synthesis of Intermediate Compound 1-d

In an argon atmosphere, Compound 1-b (30 g, 41 mmol), Compound 1-c (20.5g, 41 mmol), sodium tert-butoxide (12 g, 123 mmol), tris-tert-butylphosphine (2.0 ml, 4.2 mmol), and Pd₂dba₃ (1.9 g, 2.1 mmol) were addedto a 2 L flask and dissolved in 400 ml of toluene, and the reactionsolution was stirred at a temperature of 100° C. for 12 hours. Aftercooling, water (1 L) and ethylacetate (300 ml) were added thereto forextraction and collection of an organic layer, and was dried using MgSO₄and filtered. The filtered solution was placed under reduced pressure toremove solvent therefrom, and the obtained solid was purified andseparated by column chromatography using silica gel using CH₂Cl₂ andhexane as development solvents to thereby obtain Intermediate compound1-d (white solid, 29 g, 62%). The obtained white solid was identified byESI-LCMS as Intermediate compound 1-d.

ESI-LCMS: [M]⁺: C₈₃H₆₃N₇. 1157.5437.

Synthesis of Compound 1

In an argon atmosphere, Compound 1-d (29 g, 25 mmol) was added to a 1 Lflask, dissolved in 500 ml of o-dichlorobenzene, and was cooled to 0° C.in an ice water vessel. Boron tribromide (5 eq.) was slowly addeddropwise to the reaction solution, the temperature was slowly raised toroom temperature, and the reaction solution was stirred for 20 minutes.The reaction solution was heated to a temperature of 180° C. and stirredfor 12 hours. After cooling, triethylamine (5 ml) was slowly addeddropwise thereto to terminate the reaction and solvent was removedtherefrom under reduced pressure. The obtained solid was washed withmethanol (MeOH) and was purified and separated by column chromatographyusing silica gel using CH₂Cl₂ and hexane as development solvents tothereby obtain Compound 1 (yellow solid, 2.6 g, 9%). The obtained yellowsolid was identified by (electrospray ionization-liquid chromatographymass spectrometry (ESI-LCMS) and proton nuclear magnetic resonance(¹H-NMR) as Compound 1.

ESI-LCMS: [M]⁺: C₈₃H₅₇B₂N₇. 1173.4936.

¹H-NMR (400 MHz, CDCl₃): 10.46 (s, 1H), 9.94 (d, 2H), 9.31 (d, 1H), 8.37(d, 1H), 8.20 (d, 2H), 7.39 (m, 3H), 7.24 (m, 18H), 7.03 (m, 27H), 6.83(s, 1H), 6.49 (m, 4H).

Synthesis Example 2: Synthesis of Compound 17

Synthesis of Intermediate Compound 17-a

In an argon atmosphere, 2,6-dibromoaniline (30 g, 120 mmol),(6-(tert-butyl)pyridine-2-yl)boronic acid (45 g, 250 mmol), potassiumcarbonate (50 g, 360 mmol), and tetrakis(triphenylphosphine)palladium(0)(Pd(PPh₃)₄ in amount of 4.1 g, 3.6 mmol) were added to a 2 L flask anddissolved in 1 L of toluene and 250 ml of water, and the reactionsolution was stirred at a temperature of 120° C. for 12 hours. Aftercooling, water (1 L) and ethylacetate (300 ml) were added thereto forextraction and collection of an organic layer, and was dried using MgSO₄and filtered. The filtered solution was placed under reduced pressure toremove solvent therefrom, and the obtained solid was purified andseparated by column chromatography using silica gel using CH₂Cl₂ andhexane as development solvents to thereby obtain Intermediate compound17-a (white solid, 24 g, 57%). The obtained white solid was identifiedby ESI-LCMS and ¹H-NMR as Compound 17-a.

ESI-LCMS: [M]⁺: C₂₄H₂₉N₃. 359.2424.

¹H-NMR (400 MHz, CDCl₃): 9.30 (d, 2H), 8.30 (s, 2H), 7.73 (d, 2H), 7.29(d, 2H), 7.19 (t, 1H), 1.35 (s, 18H).

Synthesis of Intermediate Compound 17-b

In an argon atmosphere,5-chloro-N1,N1,N3,N3-tetraphenylbenzene-1,3-diamine (50 g, 112 mmol),Compound 17-a (40 g, 112 mmol), sodium tert-butoxide (32 g, 336 mmol),tris-tert-butyl phosphine (5.1 mL, 11.2 mmol), and Pd₂dba₃ (5.1 g, 5.6mmol) were added to a 2 L flask and dissolved in 1 L of o-xylene, andthe reaction solution was stirred at temperature of 140° C. for 12hours. After cooling, water (1 L) and ethylacetate (300 ml) were addedthereto for extraction and collection of an organic layer, and was driedusing MgSO₄ and filtered. The filtered solution was placed under reducedpressure to remove solvent therefrom, and the obtained solid waspurified and separated by column chromatography using silica gel usingCH₂Cl₂ and hexane as development solvents to thereby obtain Intermediatecompound 17-b (white solid, 36 g, 42%). The obtained white solid wasidentified by ESI-LCMS as Intermediate compound 17-b.

ESI-LCMS: [M]⁺: C₅₄H₅₁N₅. 769.4049.

Synthesis of Intermediate Compound 17-c

In an argon atmosphere, Compound 17-b (35 g, 45 mmol),3-bromo-iodobenzene (63 g, 227 mmol), sodium tert-butoxide (13 g, 135mmol), tris-tert-butyl phosphine (4.0 mL, 4.6 mmol), and Pd₂dba₃ (2.0 g,2.3 mmol) were added to a 2 L flask and dissolved in 450 ml of o-xylene,and the reaction solution was stirred at a temperature of 160° C. for 36hours. After cooling, water (1 L) and ethylacetate (300 ml) were addedthereto for extraction and collection of an organic layer, and was driedusing MgSO₄ and filtered. The filtered solution was placed under reducedpressure to remove solvent therefrom, and the obtained solid waspurified and separated by column chromatography using silica gel usingCH₂Cl₂ and hexane as development solvents to thereby obtain Intermediatecompound 17-c (white solid, 21 g, 51%). The obtained white solid wasidentified by ESI-LCMS as Intermediate compound 17-c.

ESI-LCMS: [M]⁺: C₆₀H₅₄N₅Br. 923.3119.

Synthesis of Intermediate Compound 17-d

In an argon atmosphere, Compound 17-c (20 g, 22 mmol), Compound 1-c (11g, 22 mmol), sodium tert-butoxide (6.3 g, 66 mmol), tris-tert-butylphosphine (1.0 mL, 2.2 mmol), and Pd₂dba₃ (1.0 g, 1.1 mmol) were addedto a 2 L flask and dissolved in 220 ml of toluene, and the reactionsolution was stirred at a temperature of 100° C. for 12 hours. Aftercooling, water (1 L) and ethylacetate (300 ml) were added thereto forextraction and collection of an organic layer, and was dried using MgSO₄and filtered. The filtered solution was placed under reduced pressure toremove solvent therefrom, and the obtained solid was purified andseparated by column chromatography using silica gel using CH₂Cl₂ andhexane as development solvents to thereby obtain Intermediate compound17-d (white solid, 21.6 g, 73%). The obtained white solid was identifiedby ESI-LCMS as Intermediate compound 17-d.

ESI-LCMS: [M]⁺: C₉₆H₈₂N₈. 1346.6071.

Synthesis of Compound 17

In an argon atmosphere, Compound 17-d (20 g, 14 mmol) was added to a 1 Lflask, dissolved in 500 ml of o-dichlorobenzene, and was cooled to 0° C.in an ice water vessel. Boron tribromide (5 eq.) was slowly addeddropwise to the reaction solution, the temperature was slowly raised toroom temperature, and the reaction solution was stirred for 20 minutes.The reaction solution was heated to a temperature of 180° C. and stirredfor 12 hours. After cooling, triethylamine (5 ml) was slowly addeddropwise thereto to terminate the reaction and solvent was removedtherefrom under reduced pressure. The obtained solid was washed withMeOH and was purified and separated by column chromatography usingsilica gel using CH₂Cl₂ and hexane as development solvents to therebyobtain Compound 17 (yellow solid, 1.4 g, 7%). The obtained yellow solidwas identified by ESI-LCMS and ¹H-NMR as Compound 17.

ESI-LCMS: [M]⁺: C₉₆H₇₆B₂N₈. 1362.6617.

¹H-NMR (400 MHz, CDCl₃): 10.52 (s, 1H), 9.83 (d, 2H), 9.41 (d, 2H), 7.39(t, 1H), 7.31 (m, 2H), 7.24 (m, 16H), 7.08 (m, 21H), 7.01 (t, 2H), 6.83(s, 1H), 6.77 (d, 2H), 6.49 (m, 4H).

Synthesis Example 3: Synthesis of Compound 31

Synthesis of Intermediate Compound 31-a

In an argon atmosphere, 3-bromo(1,1′-biphenyl)-2-amine (30 g, 120 mmol),(5-(tert-butyl)pyridine-2-yl)boronic acid (45 g, 250 mmol), potassiumcarbonate (50 g, 360 mmol), and Pd(PPh₃)₄ (4.1 g, 3.6 mmol) were addedto a 2 L flask and dissolved in 1 L of toluene and 250 ml of water, andthe reaction solution was stirred at a temperature of 120° C. for 12hours. After cooling, water (1 L) and ethylacetate (300 ml) were addedthereto for extraction and collection of an organic layer, and was driedusing MgSO₄ and filtered. The filtered solution was placed under reducedpressure to remove solvent therefrom, and the obtained solid waspurified and separated by column chromatography using silica gel usingCH₂Cl₂ and hexane as development solvents to thereby obtain Intermediatecompound 31-a (white solid, 23 g, 77%). The obtained white solid wasidentified by ESI-LCMS and ¹H-NMR as Compound 31-a.

ESI-LCMS: [M]⁺: C₁₇H₁₄N₂. 246.1238.

¹-NMR (400 MHz, CDCl₃): 9.30 (d, 1H), 8.37 (d, 1H), 8.09 (d, 1H), 7.42(m, 4H), 7.08 (m, 4H), 6.90 (t, 1H).

Synthesis of Intermediate Compound 31-b

In an argon atmosphere, Compound 31-a (30 g, 121 mmol),5-chloro-N1,N1,N3,N3-tetraphenylbenzene-1,3-diamine (54 g, 121 mmol),sodium tert-butoxide (35 g, 363 mmol), tris-tert-butyl phosphine (5.5mL, 12 mmol), and Pd₂dba₃ (5.5 g, 6.0 mmol) were added to a 2 L flaskand dissolved in 1 L of o-xylene, and the reaction solution was stirredat temperature of 140° C. for 12 hours. After cooling, water (1 L) andethylacetate (300 ml) were added thereto for extraction and collectionof an organic layer, and was dried using MgSO₄ and filtered. Thefiltered solution was placed under reduced pressure to remove solventtherefrom, and the obtained solid was purified and separated by columnchromatography using silica gel using CH₂Cl₂ and hexane as developmentsolvents to thereby obtain Intermediate compound 31-b (white solid, 43g, 58%). The obtained white solid was identified by ESI-LCMS asIntermediate compound 31-b.

ESI-LCMS: [M]⁺: C₄₇H₃₆N₄. 656.2912.

Synthesis of Intermediate Compound 31-c

In an argon atmosphere, Compound 31-b (40 g, 60 mmol),3-bromo-iodobenzene (85 g, 300 mmol), sodium tert-butoxide (58 g, 600mmol), tris-tert-butyl phosphine (2.7 ml, 6 mmol), and Pd₂dba₃ (2.7 g,3.0 mmol) were added to a 2 L flask and dissolved in 500 ml of o-xylene,and the reaction solution was stirred at a temperature of 140° C. for 36hours. After cooling, water (1 L) and ethylacetate (300 ml) were addedthereto for extraction and collection of an organic layer, and was driedusing MgSO₄ and filtered. The filtered solution was placed under reducedpressure to remove solvent therefrom, and the obtained solid waspurified and separated by column chromatography using silica gel usingCH₂Cl₂ and hexane as development solvents to thereby obtain Intermediatecompound 31-c (white solid, 30 g, 62%). The obtained white solid wasidentified by ESI-LCMS as Intermediate compound 31-c.

ESI-LCMS: [M]⁺: C₅₃H₃₉N₄Br. 810.2492.

Synthesis of Intermediate Compound 31-d

In an argon atmosphere, Mg (0.88 g, 37 mmol) was added to a 1 L flaskand was dissolved in 150 ml of anhydrous THF. A catalytic amount of 12(50 mg) was added thereto, and cooled when the color changed from blackto gray while heating to 60° C. The reaction solution was cooled to 0°C. using an water-ice vessel, Compound 31-c (30 g, 37 mmol) was addedthereto, and was stirred for 30 minutes. The reaction solution washeated to 80° C. and stirred for 30 minutes, selenium (3 eq) was addedthereto, and was stirred for 2 hours at the same temperature. Aftercooling, the reaction solution was poured in 1 L of ice water, and 1 NHCl was added dropwise thereto to adjust pH. Ethylacetate (300 ml) wasadded thereto for extraction and collection of an organic layer, and wasdried using MgSO₄ and filtered. The filtered solution was placed underreduced pressure to remove solvent therefrom, and the obtained solid waspurified and separated by column chromatography using silica gel usingCH₂Cl₂ and hexane as development solvents to thereby obtain Intermediatecompound 31-d (white solid, 11.4 g, 38%). The obtained white solid wasidentified by ESI-LCMS as Intermediate compound 31-d.

ESI-LCMS: [M]⁺: C₅₃H₄₀N₄Se. 812.1299.

Synthesis of Intermediate Compound 31-e

In an argon atmosphere, Compound 31-d (11 g, 13 mmol),1,3-dibromo-5-iodobenzene (4.9 g, 13 mmol), CuI (2.5 g, 13 mmol),2-picolinic acid (1.6 g, 13 mmol), and K₃PO₄ (14 g, 65 mmol) were addedto a 1 L flask and dissolved in 150 ml of dimethylformamide (DMF). Thereaction solution was stirred at a temperature of 160° C. for 12 hours,poured in diatomaceous earth (sold under the trade designation CELITE byImerys Minerals California, Inc. of San Jose, Calif. (hereinafter“celite”), and filtered. Ethylacetate (300 ml) was added thereto forextraction and collection of an organic layer, and was dried using MgSO₄and filtered. The filtered solution was placed under reduced pressure toremove solvent therefrom, and the obtained solid was purified andseparated by column chromatography using silica gel using CH₂Cl₂ andhexane as development solvents to thereby obtain Intermediate compound31-e (white solid, 8.4 g, 62%). The obtained white solid was identifiedby ESI-LCMS as Intermediate compound 31-e.

ESI-LCMS: [M]⁺: C₅₉H₄₂N₄SeBr₂. 1044.0917.

Synthesis of Intermediate Compound 31-f

In an argon atmosphere, Compound 31-e (8 g, 7.6 mmol),N-phenyl-2-(pyridin-2-yl)aniline (3.7 g, 15 mmol), sodium tert-butoxide(2.2 g, 23 mmol), tris-tert-butyl phosphine (0.4 mL, 6.8 mmol), andPd₂dba₃ (0.34 g, 3.4 mmol) were added to a 2 L flask and dissolved in100 ml of toluene, and the reaction solution was stirred at atemperature of 140° C. for 12 hours. After cooling, water (1 L) andethylacetate (300 ml) were added thereto for extraction and collectionof an organic layer, and was dried using MgSO₄ and filtered. Thefiltered solution was placed under reduced pressure to remove solventtherefrom, and the obtained solid was purified and separated by columnchromatography using silica gel using CH₂Cl₂ and hexane as developmentsolvents to thereby obtain Intermediate compound 31-f (white solid, 7.5g, 72%). The obtained white solid was identified by ESI-LCMS asIntermediate compound 31-f.

ESI-LCMS: [M]⁺: C₉₃H₆₈N₈Se. 1376.4669.

Synthesis of Compound 31

In an argon atmosphere, Compound 31-f (7.5 g, 5.4 mmol) was added to a 1L flask, dissolved in 200 ml of o-dichlorobenzene, and was cooled to 0°C. in an ice water vessel. Boron tribromide (5 eq.) was slowly addeddropwise to the reaction solution, the temperature was slowly raised toroom temperature, and the reaction solution was stirred for 20 minutes.The reaction solution was heated to a temperature of 180° C. and stirredfor 12 hours. After cooling, triethylamine (5 ml) was slowly addeddropwise thereto to terminate the reaction and solvent was removedtherefrom under reduced pressure. The obtained solid was washed withMeOH and purified and separated by column chromatography using silicagel using CH₂Cl₂ and hexane as development solvents to thereby obtainCompound 31 (yellow solid, 0.8 g, 11%). The obtained yellow solid wasidentified by ESI-LCMS and ¹H-NMR as Compound 31.

ESI-LCMS: [M]⁺: C₉₃H₆₂B₂N₈Se. 1395.4434.

¹H-NMR (400 MHz, CDCl₃): 10.26 (s, 1H), 9.65 (d, 2H), 9.41 (d, 2H), 9.31(d, 2H), 8.37 (d, 3H), 8.20 (m, 1H), 7.39 (m, 10H), 7.24 (m, 12H), 7.08(m, 24H), 6.77 (s, 1H), 7.01 (t, 2H), 6.49 (s, 2H).

Synthesis Example 4: Synthesis of Compound 37

Synthesis of Intermediate Compound 37-a

In an argon atmosphere,5-fluoro-N1,N1,N3,N3-tetraphenylbenzene-1,3-diamine (50 g, 116 mmol),resorcinol (6.4 g, 58 mmol), and potassium hydroxide (KOH) (6.5 g, 116mmol) were added to a 2 L flask and dissolved in 1 L of dimethylsulfoxide (DMSO), and the reaction solution was stirred at a temperatureof 180° C. for 12 hours. After cooling, water (1 L) and ethylacetate(300 ml) were added thereto for extraction and collection of an organiclayer, and was dried using MgSO₄ and filtered. The filtered solution wasplaced under reduced pressure to remove solvent therefrom, and theobtained solid was purified and separated by column chromatography usingsilica gel using CH₂Cl₂ and hexane as development solvents to therebyobtain Intermediate compound 37-a (white solid, 34 g, 64%). The obtainedwhite solid was identified by ESI-LCMS as Intermediate compound 37-a.

ESI-LCMS: [M]⁺: C₆₆H₅₀N₄O₂. 930.3912.

Synthesis of Intermediate Compound 37-b

In an argon atmosphere, Compound 37-a (30 g, 32 mmol) was added to a 1 Lflask and dissolved in 300 ml of anhydrous oxolane (THF). After coolingto −78° C., N-butyllithium (n-BuLi) (1.2 eq.) was slowly added dropwisethereto for 30 minutes. Then, the reaction solution was heated to roomtemperature and stirred for 2 hours, cooled to −78° C. again, trimethylborate (1.5 eq.) was added thereto, and stirred at room temperature for12 hours. 300 ml of 0.1N hydrochloric acid (HCl) was poured to thereaction solution to terminate the reaction, ethylacetate (300 ml) wasadded thereto to collect an organic layer, and the reaction solution wasdried using MgSO₄ and filtered. Solvent was removed from the filteredsolution under reduced pressure, and the solid obtained therefrom wasrecrystallized using hexane to thereby obtain Intermediate compound 37-b(white solid, 16 g, 55%). The obtained white solid was identified byESI-LCMS as Intermediate compound 37-b.

ESI-LCMS: [M]⁺: C₆₆H₅₁N₄O₄B. 974.4001.

Synthesis of Intermediate Compound 37-c

In an argon atmosphere, Compound 37-b (16 g, 16 mmol),2,2′-(2-bromo-1,3-phenylene)dipyridine (5.1 g, 16 mmol), potassiumcarbonate (6.6 g, 48 mmol), and Pd(PPh₃)₄ (0.55 g, 0.5 mmol) were addedto a 1 L flask and dissolved in 150 ml of toluene and 50 ml of water,and the reaction solution was stirred at a temperature of 120° C. for 12hours. After cooling, water (1 L) and ethylacetate (300 ml) were addedthereto for extraction and collection of an organic layer, and was driedusing MgSO₄ and filtered. The filtered solution was placed under reducedpressure to remove solvent therefrom, and the obtained solid waspurified and separated by column chromatography using silica gel usingCH₂Cl₂ and hexane as development solvents to thereby obtain Intermediatecompound 37-c (white solid, 14 g, 74%). The obtained white solid wasidentified by ESI-LCMS as Intermediate compound 37-c.

ESI-LCMS: [M]⁺: C₈₂H₆₀N₆O₂. 1160.4884.

Synthesis of Compound 37

In an argon atmosphere, Compound 37-c (14 g, 12 mmol) was added to a 1 Lflask, dissolved in 300 ml of o-dichlorobenzene, and was cooled to 0° C.in an ice water vessel. Boron tribromide (5 eq.) was slowly addeddropwise to the reaction solution, the temperature was slowly raised toroom temperature, and the reaction solution was stirred for 20 minutes.The reaction solution was heated to a temperature of 180° C. and stirredfor 12 hours. After cooling, triethylamine (5 ml) was slowly addeddropwise thereto to terminate the reaction and solvent was removedtherefrom under reduced pressure. The obtained solid was washed withMeOH and was purified and separated by column chromatography usingsilica gel using CH₂Cl₂ and hexane as development solvents to therebyobtain Compound 37 (yellow solid, 1.7 g, 12%). The obtained yellow solidwas identified by ESI-LCMS and ¹H-NMR as Compound 37.

ESI-LCMS: [M]⁺: C₈₂H₅₄B₂N₆O₂. 1176.0157.

¹H-NMR (400 MHz, CDCl₃): 10.31 (s, 1H), 9.42 (d, 2H), 8.45 (d, 2H), 8.37(d, 2H), 7.83 (t, 1H), 7.38 (m, 4H), 7.24 (m, 12H), 7.08 (m, 12H), 6.90(m, 9H), 6.83 (t, 1H), 6.52 (d, 4H).

Synthesis Example 5: Synthesis of Compound 41

Synthesis of Intermediate Compound 41-a

In an argon atmosphere, 3,5-dibromo-fluorobenzene (50 g, 197 mmol),resorcinol (10 g, 90 mmol), and KOH (11.7 g, 180 mmol) were added to a 2L flask and dissolved in 1 L of DMSO, and the reaction solution wasstirred at a temperature of 180° C. for 12 hours. After cooling, water(1 L) and ethylacetate (300 ml) were added thereto for extraction andcollection of an organic layer, and was dried using MgSO₄ and filtered.The filtered solution was placed under reduced pressure to removesolvent therefrom, and the obtained solid was purified and separated bycolumn chromatography using silica gel using CH₂Cl₂ and hexane asdevelopment solvents to thereby obtain Intermediate compound 41-a (whitesolid, 22 g, 43%). The obtained white solid was identified by ESI-LCMSand ¹H-NMR as Intermediate compound 41-a.

ESI-LCMS: [M]⁺: C₁₈H₁₀Br₄O₂. 573.7473.

¹H-NMR (400 MHz, CDCl₃): 7.70 (s, 2H), 7.28 (m, 5H), 7.00 (d, 2H), 6.52(s, 1H).

Synthesis of Intermediate Compound 41-b

In an argon atmosphere, Compound 41-a (20 g, 35 mmol),N-phenyl-2-(pyridin-2-yl)aniline (51 g, 207 mmol), sodium tert-butoxide(10 g, 105 mmol), tris-tert-butyl phosphine (0.4 mL, 7.0 mmol), andPd₂dba₃ (0.34 g, 3.5 mmol) were added to a 2 L flask and dissolved in500 ml of toluene, and the reaction solution was stirred at atemperature of 110° C. for 12 hours. After cooling, water (1 L) andethylacetate (300 ml) were added thereto for extraction and collectionof an organic layer, and was dried using MgSO₄ and filtered. Thefiltered solution was placed under reduced pressure to remove solventtherefrom, and the obtained solid was purified and separated by columnchromatography using silica gel using CH₂Cl₂ and hexane as developmentsolvents to thereby obtain Intermediate compound 41-b (white solid, 22.5g, 52%). The obtained white solid was identified by ESI-LCMS asIntermediate compound 41-b.

ESI-LCMS: [M]⁺: C₈₆H₆₂N₈O₂. 1238.5001.

Synthesis of Compound 41

In an argon atmosphere, Compound 41-b (20 g, 16 mmol) was added to a 1 Lflask, dissolved in 500 ml of o-dichlorobenzene, and was cooled to 0° C.in an ice water vessel. Boron tribromide (5 eq.) was slowly addeddropwise to the reaction solution, the temperature was slowly raised toroom temperature, and the reaction solution was stirred for 20 minutes.The reaction solution was heated to a temperature of 180° C. and stirredfor 12 hours. After cooling, triethylamine (5 ml) was slowly addeddropwise thereto to terminate the reaction and solvent was removedtherefrom under reduced pressure. The obtained solid was washed withMeOH and was purified and separated by column chromatography usingsilica gel using CH₂Cl₂ and hexane as development solvents to therebyobtain Compound 41 (yellow solid, 1.6 g, 8%). The obtained yellow solidwas identified by ESI-LCMS and ¹H-NMR as Compound 41.

ESI-LCMS: [M]⁺: C₈₆H₅₆B₂N₈O₂. 1254.4644.

¹H-NMR (400 MHz, CDCl₃): 10.78 (s, 1H), 9.87 (d, 2H), 9.31 (d, 4H), 8.37(d, 4H), 7.39 (m, 12H), 7.21 (m, 8H), 7.04 (m, 24H), 6.65 (s, 1H), 6.50(d, 4H).

Synthesis Example 6: Synthesis of Compound 50

Synthesis of Intermediate Compound 50-a

In an argon atmosphere, 3,5-dibromo-fluorobenzene (23 g, 90 mmol),phenol (8.5 g, 90 mmol), and KOH (11.7 g, 180 mmol) were added to a 2 Lflask and dissolved in 1 L of DMSO, and the reaction solution wasstirred at a temperature of 180° C. for 12 hours. After cooling, water(1 L) and ethylacetate (300 ml) were added thereto for extraction andcollection of an organic layer, and was dried using MgSO₄ and filtered.The filtered solution was placed under reduced pressure to removesolvent therefrom, and the obtained solid was purified and separated bycolumn chromatography using silica gel using CH₂Cl₂ and hexane asdevelopment solvents to thereby obtain Intermediate compound 50-a (whitesolid, 22.6 g, 77%). The obtained white solid was identified by ESI-LCMSand ¹H-NMR as Intermediate compound 50-a.

ESI-LCMS: [M]⁺: C₁₂H₈Br₂O. 325.8924.

Synthesis of Intermediate Compound 50-b

In an argon atmosphere, 2,6-dibromoaniline (30 g, 120 mmol), 2-pyridinylboronic acid (29 g, 240 mmol), potassium carbonate (50 g, 360 mmol), andPd(PPh₃)₄ (4.1 g, 3.6 mmol) were added to a 2 L flask and dissolved in 1L of toluene and 250 ml of water, and the reaction solution was stirredat a temperature of 120° C. for 12 hours. After cooling, water (1 L) andethylacetate (300 ml) were added thereto for extraction and collectionof an organic layer, and was dried using MgSO₄ and filtered. Thefiltered solution was placed under reduced pressure to remove solventtherefrom, and the obtained solid was purified and separated by columnchromatography using silica gel using CH₂Cl₂ and hexane as developmentsolvents to thereby obtain Intermediate compound 50-b (white solid, 24g, 81%). The obtained white solid was identified by ESI-LCMS asIntermediate compound 50-b.

ESI-LCMS: [M]⁺: C₁₆H₁₃N₃. 247.1114.

Synthesis of Intermediate Compound 50-c

In an argon atmosphere, Compound 50-a (26 g, 80 mmol), Compound 50-b (20g, 80 mmol), sodium tert-butoxide (23 g, 240 mmol), tris-tert-butylphosphine (3.6 ml, 8.0 mmol), and Pd₂dba₃ (3.6 g, 4 mmol) were added toa 2 L flask and dissolved in 800 ml of toluene, and the reactionsolution was stirred at a temperature of 110° C. for 12 hours. Aftercooling, water (1 L) and ethylacetate (300 ml) were added thereto forextraction and collection of an organic layer, and was dried using MgSO₄and filtered. The filtered solution was placed under reduced pressure toremove solvent therefrom, and the obtained solid was purified andseparated by column chromatography using silica gel using CH₂Cl₂ andhexane as development solvents to thereby obtain Intermediate compound50-c (white solid, 22.4 g, 67%). The obtained white solid was identifiedby ESI-LCMS as Intermediate compound 50-c.

ESI-LCMS: [M]⁺: C₂₂H₁₆N₃OBr. 417.0443.

Synthesis of Intermediate Compound 50-d

In an argon atmosphere, Compound 50-c (20 g, 48 mmol),benzene-1,3-dithiol (3.4 g, 24 mmol), copper iodide (CuI) (4.5 g, 24mmol), 2-picolinic acid (3 g, 24 mmol), and K₃PO₄ (17 g, 72 mmol) wereadded to a 1 L flask and dissolved in 500 ml of DMF. The reactionsolution was stirred at a temperature of 160° C. for 12 hours, poured incelite, and filtered. Ethylacetate (300 ml) was added thereto forextraction and collection of an organic layer, and was dried using MgSO₄and filtered. The filtered solution was placed under reduced pressure toremove solvent therefrom, and the obtained solid was purified andseparated by column chromatography using silica gel using CH₂Cl₂ andhexane as development solvents to thereby obtain Intermediate compound50-d (white solid, 15 g, 58%). The obtained white solid was identifiedby ESI-LCMS as Intermediate compound 50-d.

ESI-LCMS: [M]⁺: C₇₄H₅₂N₆S₂O₂. 1120.3636.

Synthesis of Compound 50

In an argon atmosphere, Compound 50-d (20 g, 13 mmol) was added to a 1 Lflask, dissolved in 500 ml of o-dichlorobenzene, and was cooled to 0° C.in an ice water vessel. Boron tribromide (5 eq.) was slowly addeddropwise to the reaction solution, the temperature was slowly raised toroom temperature, and the reaction solution was stirred for 20 minutes.The reaction solution was heated to a temperature of 180° C. and stirredfor 12 hours. After cooling, triethylamine (5 ml) was slowly addeddropwise thereto to terminate the reaction and solvent was removedtherefrom under reduced pressure. The obtained solid was washed withMeOH and purified and separated by column chromatography using silicagel using CH₂Cl₂ and hexane as development solvents to thereby obtainCompound 50 (yellow solid, 0.9 g, 6%). The obtained yellow solid wasidentified by ESI-LCMS and ¹H-NMR as Compound 50.

ESI-LCMS: [M]⁺: C₇₄H₄₆B₂N₆O₂S₂. 1136.3336.

¹H-NMR (400 MHz, CDCl₃): 10.56 (s, 1H), 9.76 (d, 2H), 9.41 (d, 4H), 8.37(d, 4H), 7.41 (m, 6H), 7.27 (m, 8H), 7.12 (m, 14H), 6.88 (s, 2H).

Synthesis Example 7: Synthesis of Compound 55

Synthesis of Intermediate Compound 55-a

In an argon atmosphere, [1,1′:3′,1″-terphenyl]-2′-amine (30 g, 122mmol), 5-chloro-N1,N1,N3,N3-tetraphenylbenzene-1,3-diamine (58 g, 122mmol), sodium tert-butoxide (35 g, 363 mmol), tris-tert-butyl phosphine(5.5 mL, 12 mmol), and Pd₂dba₃ (5.5 g, 6.0 mmol) were added to a 2 Lflask and dissolved in 1 L of o-xylene, and the reaction solution wasstirred at a temperature of 140° C. for 12 hours. After cooling, water(1 L) and ethylacetate (300 ml) were added thereto for extraction andcollection of an organic layer, and was dried using MgSO₄ and filtered.The filtered solution was placed under reduced pressure to removesolvent therefrom, and the obtained solid was purified and separated bycolumn chromatography using silica gel using CH₂Cl₂ and hexane asdevelopment solvents to thereby obtain Intermediate compound 55-a (whitesolid, 44.8 g, 66%). The obtained white solid was identified by ESI-LCMSas Intermediate compound 55-a.

ESI-LCMS: [M]⁺: C₄₈H₃₇N₃. 655.3001.

Synthesis of Intermediate Compound 55-b

In an argon atmosphere, Compound 55-a (40 g, 61 mmol),3-bromo-iodobenzene (170 g, 610 mmol), sodium tert-butoxide (17.5 g, 183mmol), tris-tert-butyl phosphine (2.8 mL, 6.1 mmol), and Pd₂dba₃ (2.8 g,3.1 mmol) were added to a 2 L flask and dissolved in 200 ml of o-xylene,and the reaction solution was stirred at a temperature of 140° C. for 36hours. After cooling, water (1 L) and ethylacetate (300 ml) were addedthereto for extraction and collection of an organic layer, and was driedusing MgSO₄ and filtered. The filtered solution was placed under reducedpressure to remove solvent therefrom, and the obtained solid waspurified and separated by column chromatography using silica gel usingCH₂Cl₂ and hexane as development solvents to thereby obtain Intermediatecompound 55-b (white solid, 22 g, 45%). The obtained white solid wasidentified by ESI-LCMS as Intermediate compound 55-b.

ESI-LCMS: [M]⁺: C₅₄H₄₀N₃Br. 809.2412.

Synthesis of Intermediate Compound 55-c

In an argon atmosphere, Compound 55-b (22 g, 27 mmol),1,3,5-dichlorobenzenethiol (4.9 g, 27 mmol), CuI (5.1 g, 27 mmol),2-picolinic acid (3.3 g, 27 mmol), and K₃PO₄ (20 g, 81 mmol) were addedto a 1 L flask and dissolved in 250 ml of DMF. The reaction solution wasstirred at a temperature of 160° C. for 12 hours, poured in celite, andfiltered. Ethylacetate (300 ml) was added thereto for extraction andcollection of an organic layer, and was dried using MgSO₄ and filtered.The filtered solution was placed under reduced pressure to removesolvent therefrom, and the obtained solid was purified and separated bycolumn chromatography using silica gel using CH₂Cl₂ and hexane asdevelopment solvents to thereby obtain Intermediate compound 55-c (whitesolid, 14 g, 56%). The obtained white solid was identified by ESI-LCMSas Intermediate compound 55-c.

ESI-LCMS: [M]⁺: C₆₀H₄₃N₃Cl₂S. 907.2612.

Synthesis of Intermediate Compound 55-d

In an argon atmosphere, Compound 55-c (14 g, 15 mmol),N-phenyl-2-(pyridin-2-yl)aniline (3.8 g, 15 mmol), sodium tert-butoxide(43.5 g, 45 mmol), tris-tert-butyl phosphine (1.5 mL, 1.4 mmol), andPd₂dba₃ (0.7 g, 0.8 mmol) were added to a 1 L flask and dissolved in 150ml of o-xylene, and the reaction solution was stirred at a temperatureof 140° C. for 36 hours. After cooling, water (1 L) and ethylacetate(300 ml) were added thereto for extraction and collection of an organiclayer, and was dried using MgSO₄ and filtered. The filtered solution wasplaced under reduced pressure to remove solvent therefrom, and theobtained solid was purified and separated by column chromatography usingsilica gel using CH₂Cl₂ and hexane as development solvents to therebyobtain Intermediate compound 55-d (white solid, 15 g, 77%). The obtainedwhite solid was identified by ESI-LCMS as Intermediate compound 55-d.

ESI-LCMS: [M]⁺: C₉₄H₆₉N₇S. 1327.5353.

Synthesis of Compound 55

In an argon atmosphere, Compound 55-d (15 g, 11 mmol) was added to a 1 Lflask, dissolved in 500 ml of o-dichlorobenzene, and was cooled to 0° C.in an ice water vessel. Boron tribromide (5 eq.) was slowly addeddropwise to the reaction solution, the temperature was slowly raised toroom temperature, and the reaction solution was stirred for 20 minutes.The reaction solution was heated to a temperature of 180° C. and stirredfor 12 hours. After cooling, triethylamine (5 ml) was slowly addeddropwise thereto to terminate the reaction and solvent was removedtherefrom under reduced pressure. The obtained solid was washed withMeOH and was purified and separated by column chromatography usingsilica gel using CH₂Cl₂ and hexane as development solvents to therebyobtain Compound 55 (yellow solid, 1.2 g, 8%). The obtained yellow solidwas identified by ESI-LCMS and ¹H-NMR as Compound 55.

ESI-LCMS: [M]⁺: C₉₄H₆₃B₂N₇S. 1343.5001.

¹H-NMR (400 MHz, CDCl₃): 10.43 (s, 1H), 9.58 (d, 2H), 9.31 (d, 2H), 8.37(d, 2H), 8.20 (d, 2H), 7.76 (s, 1H), 7.41 (m, 7H), 7.25 (m, 13H), 7.12(m, 17H), 6.57 (s, 1H), 6.49 (s, 2H).

Synthesis Example 8: Synthesis of Compound 57

Synthesis of Intermediate Compound 57-a

In an argon atmosphere, Compound 55-b (30 g, 37 mmol), aniline (3.5 g,37 mmol), sodium tert-butoxide (10.6 g, 111 mmol), tris-tert-butylphosphine (1.7 ml, 3.8 mmol), and Pd₂dba₃ (1.7 g, 1.9 mmol) were addedto a 1 L flask and dissolved in 400 ml of o-xylene, and the reactionsolution was stirred at a temperature of 140° C. for 12 hours. Aftercooling, water (1 L) and ethylacetate (300 ml) were added thereto forextraction and collection of an organic layer, and was dried using MgSO₄and filtered. The filtered solution was placed under reduced pressure toremove solvent therefrom, and the obtained solid was purified andseparated by column chromatography using silica gel using CH₂Cl₂ andhexane as development solvents to thereby obtain Intermediate compound57-a (white solid, 20 g, 68%). The obtained white solid was identifiedby ESI-LCMS as Intermediate compound 57-a.

ESI-LCMS: [M]⁺: C₆₀H₄₆N₄. 822.3734.

Synthesis of Intermediate Compound 57-b

In an argon atmosphere, Compound 57-a (20 g, 24 mmol),1,3-dichloro-5-bromobenzene (3.5 g, 37 mmol), sodium tert-butoxide (6.9g, 72 mmol), tris-tert-butyl phosphine (1.1 ml, 2.4 mmol), and Pd₂dba₃(1.1 g, 1.2 mmol) were added to a 1 L flask and dissolved in 250 ml ofo-xylene, and the reaction solution was stirred at a temperature of 140°C. for 12 hours. After cooling, water (1 L) and ethylacetate (300 ml)were added thereto for extraction and collection of an organic layer,and was dried using MgSO₄ and filtered. The filtered solution was placedunder reduced pressure to remove solvent therefrom, and the obtainedsolid was purified and separated by column chromatography using silicagel using CH₂Cl₂ and hexane as development solvents to thereby obtainIntermediate compound 57-b (white solid, 15 g, 65%). The obtained whitesolid was identified by ESI-LCMS as Intermediate compound 57-b.

ESI-LCMS: [M]⁺: C₆₆H₄₈N₄Cl₂. 966.3311.

Synthesis of Intermediate Compound 57-c

In an argon atmosphere, Compound 57-b (15 g, 15 mmol),N-phenyl-2-(pyridin-2-yl)aniline (7.6 g, 30 mmol), sodium tert-butoxide(4.3 g, 45 mmol), tris-tert-butyl phosphine (0.7 mL, 1.6 mmol), andPd₂dba₃ (0.7 g, 0.8 mmol) were added to a 1 L flask and dissolved in 150ml of o-xylene, and the reaction solution was stirred at a temperatureof 140° C. for 12 hours. After cooling, water (1 L) and ethylacetate(300 ml) were added thereto for extraction and collection of an organiclayer, and was dried using MgSO₄ and filtered. The filtered solution wasplaced under reduced pressure to remove solvent therefrom, and theobtained solid was purified and separated by column chromatography usingsilica gel using CH₂Cl₂ and hexane as development solvents to therebyobtain Intermediate compound 57-c (white solid, 12 g, 59%). The obtainedwhite solid was identified by ESI-LCMS as Intermediate compound 57-c.

ESI-LCMS: [M]⁺: C₁₀₀H₇₄N₈. 1386.5997.

Synthesis of Compound 57

In an argon atmosphere, Compound 57-c (12 g, 8 mmol) was added to a 1 Lflask, dissolved in 500 ml of o-dichlorobenzene, and cooled to 0° C. inan ice water vessel. Boron tribromide (5 eq.) was slowly added dropwiseto the reaction solution, the temperature was slowly raised to roomtemperature, and the reaction solution was stirred for 20 minutes. Thereaction solution was heated to a temperature of 180° C. and stirred for12 hours. After cooling, triethylamine (5 ml) was slowly added dropwisethereto to terminate the reaction and solvent was removed therefromunder reduced pressure. The obtained solid was washed with MeOH and waspurified and separated by column chromatography using silica gel usingCH₂Cl₂ and hexane as development solvents to thereby obtain Compound 57(yellow solid, 1.1 g, 9%). The obtained yellow solid was identified byESI-LCMS and ¹H-NMR as Compound 57.

ESI-LCMS: [M]⁺: C₁₀₀H₆₈B₂N₈. 1402.5554.

¹H-NMR (400 MHz, CDCl₃): 10.59 (s, 1H), 9.68 (d, 2H), 9.31 (d, 2H), 8.37(d, 2H), 8.20 (d, 2H), 7.76 (s, 1H), 7.43 (m, 9H), 7.27 (m, 21H), 7.12(m, 17H), 7.03 (m, 7H), 6.83 (s, 1H), 6.49 (s, 4H).

Synthesis Example 9: Synthesis of Compound 82

Synthesis of Intermediate Compound 82-a

In an argon atmosphere, Compound 55-b (30 g, 37 mmol), 2-amino biphenyl(6.3 g, 37 mmol), sodium tert-butoxide (10.6 g, 111 mmol),tris-tert-butyl phosphine (1.7 ml, 3.8 mmol), and Pd₂dba₃ (1.7 g, 1.9mmol) were added to a 1 L flask and dissolved in 400 ml of o-xylene, andthe reaction solution was stirred at a temperature of 140° C. for 12hours. After cooling, water (1 L) and ethylacetate (300 ml) were addedthereto for extraction and collection of an organic layer, and was driedusing MgSO₄ and filtered. The filtered solution was placed under reducedpressure to remove solvent therefrom, and the obtained solid waspurified and separated by column chromatography using silica gel usingCH₂Cl₂ and hexane as development solvents to thereby obtain Intermediatecompound 82-a (white solid, 24 g, 74%). The obtained white solid wasidentified by ESI-LCMS as Intermediate compound 82-a.

ESI-LCMS: [M]⁺: C₆₆H₅₀N₄. 898.4006.

Synthesis of Intermediate Compound 82-b

In an argon atmosphere, Compound 82-a (24 g, 27 mmol),1,3-dichloro-5-bromobenzene (6 g, 27 mmol), sodium tert-butoxide (7.8 g,81 mmol), tris-tert-butyl phosphine (1.2 ml, 2.8 mmol), and Pd₂dba₃ (1.2g, 1.4 mmol) were added to a 1 L flask and dissolved in 300 ml ofo-xylene, and the reaction solution was stirred at a temperature of 100°C. for 12 hours. After cooling, water (1 L) and ethylacetate (300 ml)were added thereto for extraction and collection of an organic layer,and was dried using MgSO₄ and filtered. The filtered solution was placedunder reduced pressure to remove solvent therefrom, and the obtainedsolid was purified and separated by column chromatography using silicagel using CH₂Cl₂ and hexane as development solvents to thereby obtainIntermediate compound 82-b (white solid, 18 g, 65%). The obtained whitesolid was identified by ESI-LCMS as Intermediate compound 82-b.

ESI-LCMS: [M]⁺: C₇₂H₅₂N₄Cl₂. 1042.2437.

Synthesis of Intermediate Compound 82-c

In an argon atmosphere, Compound 82-b (18 g, 17 mmol),N-phenyl-[1,1′-biphenyl]-2-amine (8.5 g, 34 mmol), sodium tert-butoxide(4.9 g, 51 mmol), tris-tert-butyl phosphine (1.0 ml, 1.8 mmol), andPd₂dba₃ (0.8 g, 0.9 mmol) were added to a 1 L flask and dissolved in 200ml of o-xylene, and the reaction solution was stirred at a temperatureof 140° C. for 12 hours. After cooling, water (1 L) and ethylacetate(300 ml) were added thereto for extraction and collection of an organiclayer, and was dried using MgSO₄ and filtered. The filtered solution wasplaced under reduced pressure to remove solvent therefrom, and theobtained solid was purified and separated by column chromatography usingsilica gel using CH₂Cl₂ and hexane as development solvents to therebyobtain Intermediate compound 82-c (white solid, 17 g, 71%). The obtainedwhite solid was identified by ESI-LCMS as Intermediate compound 82-c.

ESI-LCMS: [M]⁺: C₁₀₈H₈₀N₆. 1460.6318.

Synthesis of Compound 82

In an argon atmosphere, Compound 82-c (17 g, 12 mmol) was added to a 1 Lflask, dissolved in 500 ml of o-dichlorobenzene, and cooled to 0° C. inan ice water vessel. Boron tribromide (5 eq.) was slowly added dropwiseto the reaction solution, the temperature was slowly raised to roomtemperature, and the reaction solution was stirred for 20 minutes. Thereaction solution was heated to a temperature of 180° C. and stirred for12 hours. After cooling, triethylamine (5 ml) was slowly added dropwisethereto to terminate the reaction and solvent was removed therefromunder reduced pressure. The obtained solid was washed with MeOH and waspurified and separated by column chromatography using silica gel usingCH₂Cl₂ and hexane as development solvents to thereby obtain Compound 82(yellow solid, 1.9 g, 11%). The obtained yellow solid was identified byESI-LCMS and ¹H-NMR as Compound 82.

ESI-LCMS: [M]⁺: C₁₀₈H₇₄B₂N₆. 1476.6551.

¹H-NMR (400 MHz, CDCl₃): 10.36 (s, 1H), 9.22 (d, 2H), 8.20 (d, 2H), 8.10(d, 3H), 7.43 (m, 13H), 7.24 (m, 16H), 7.12 (m, 20H), 7.01 (m, 7H), 6.87(s, 1H), 6.52 (s, 4H).

Synthesis Example 10: Synthesis of Compound 83

Synthesis of Intermediate Compound 83-a

In an argon atmosphere, 3,5-dibromo-chlorobenzene (18 g, 111 mmol),N-phenyl-[1,1′-biphenyl]-2-amine (54 g, 222 mmol), sodium tert-butoxide(32 g, 333 mmol), tris-tert-butyl phosphine (5.0 ml, 11 mmol), andPd₂dba₃ (5.1 g, 5.5 mmol) were added to a 2 L flask and dissolved in 1 Lof o-xylene, and the reaction solution was stirred at temperature of100° C. for 12 hours. After cooling, water (1 L) and ethylacetate (300ml) were added thereto for extraction and collection of an organiclayer, and was dried using MgSO₄ and filtered. The filtered solution wasplaced under reduced pressure to remove solvent therefrom, and theobtained solid was purified and separated by column chromatography usingsilica gel using CH₂Cl₂ and hexane as development solvents to therebyobtain Intermediate compound 83-a (white solid, 50 g, 75%). The obtainedwhite solid was identified by ESI-LCMS as Intermediate compound 83-a.

ESI-LCMS: [M]⁺: C₄₂H₃₁N₂Cl. 598.2201.

Synthesis of Intermediate Compound 83-b

In an argon atmosphere, Compound 83-a (50 g, 83 mmol), aniline (8 g, 83mmol), sodium tert-butoxide (24 g, 249 mmol), tris-tert-butyl phosphine(4 ml, 8.4 mmol), and Pd₂dba₃ (3.8 g, 4.2 mmol) were added to a 2 Lflask and dissolved in 800 ml of o-xylene, and the reaction solution wasstirred at a temperature of 140° C. for 12 hours. After cooling, water(1 L) and ethylacetate (300 ml) were added thereto for extraction andcollection of an organic layer, and was dried using MgSO₄ and filtered.The filtered solution was placed under reduced pressure to removesolvent therefrom, and the obtained solid was purified and separated bycolumn chromatography using silica gel using CH₂Cl₂ and hexane asdevelopment solvents to thereby obtain Intermediate compound 83-b (whitesolid, 38 g, 71%). The obtained white solid was identified by ESI-LCMSas Intermediate compound 83-b.

ESI-LCMS: [M]⁺: C₄₈H₃₇N₃. 655.3001.

Synthesis of Intermediate Compound 83-c

In an argon atmosphere, Compound 83-a (50 g, 83 mmol),[1,1′:3′,1″-terphenyl]-2′-amine (20 g, 83 mmol), sodium tert-butoxide(24 g, 249 mmol), tris-tert-butyl phosphine (4 ml, 8.4 mmol), andPd₂dba₃ (3.8 g, 4.2 mmol) were added to a 2 L flask and dissolved in 800ml of o-xylene, and the reaction solution was stirred at a temperatureof 140° C. for 12 hours. After cooling, water (1 L) and ethylacetate(300 ml) were added thereto for extraction and collection of an organiclayer, and was dried using MgSO₄ and filtered. The filtered solution wasplaced under reduced pressure to remove solvent therefrom, and theobtained solid was purified and separated by column chromatography usingsilica gel using CH₂Cl₂ and hexane as development solvents to therebyobtain Intermediate compound 83-c (white solid, 49 g, 73%). The obtainedwhite solid was identified by ESI-LCMS as Intermediate compound 83-c.

ESI-LCMS: [M]⁺: C₆₀H₄₅N₃. 807.3535.

Synthesis of Intermediate Compound 83-d

In an argon atmosphere, Compound 83-c (45 g, 55 mmol),3-bromo-iodobenzene (15.8 g, 55 mmol), sodium tert-butoxide (16 g, 165mmol), tris-tert-butyl phosphine (2.5 ml, 5.6 mmol), and Pd₂dba₃ (2.5 g,2.8 mmol) were added to a 2 L flask and dissolved in 800 ml of o-xylene,and the reaction solution was stirred at a temperature of 100° C. for 12hours. After cooling, water (1 L) and ethylacetate (300 ml) were addedthereto for extraction and collection of an organic layer, and was driedusing MgSO₄ and filtered. The filtered solution was placed under reducedpressure to remove solvent therefrom, and the obtained solid waspurified and separated by column chromatography using silica gel usingCH₂Cl₂ and hexane as development solvents to thereby obtain Intermediatecompound 83-d (white solid, 35 g, 67%). The obtained white solid wasidentified by ESI-LCMS as Intermediate compound 83-d.

ESI-LCMS: [M]⁺: C₆₆H₄₈N₃Br. 961.2738.

Synthesis of Intermediate Compound 83-e

In an argon atmosphere, Compound 83-d (35 g, 36 mmol), Compound 83-b(23.6 g, 36 mmol), sodium tert-butoxide (10 g, 108 mmol),tris-tert-butyl phosphine (1.6 ml, 3.6 mmol), and Pd₂dba₃ (1.6 g, 1.8mmol) were added to a 2 L flask and dissolved in 800 ml of o-xylene, andthe reaction solution was stirred at a temperature of 140° C. for 12hours. After cooling, water (1 L) and ethylacetate (300 ml) were addedthereto for extraction and collection of an organic layer, and was driedusing MgSO₄ and filtered. The filtered solution was placed under reducedpressure to remove solvent therefrom, and the obtained solid waspurified and separated by column chromatography using silica gel usingCH₂Cl₂ and hexane as development solvents to thereby obtain Intermediatecompound 83-e (white solid, 32 g, 59%). The obtained white solid wasidentified by ESI-LCMS as Intermediate compound 83-e.

ESI-LCMS: [M]⁺: C₁₁₄H₈₄N₆. 1536.6656.

Synthesis of Compound 83

In an argon atmosphere, Compound 83-e (32 g, 20 mmol) was added to a 1 Lflask, dissolved in 500 ml of o-dichlorobenzene, and cooled to 0° C. inan ice water vessel. Boron tribromide (5 eq.) was slowly added dropwiseto the reaction solution, the temperature was slowly raised to roomtemperature, and the reaction solution was stirred for 20 minutes. Thereaction solution was heated to a temperature of 180° C. and stirred for12 hours. After cooling, triethylamine (5 ml) was slowly added dropwisethereto to terminate the reaction and solvent was removed therefromunder reduced pressure. The obtained solid was washed with MeOH and waspurified and separated by column chromatography using silica gel usingCH₂Cl₂ and hexane as development solvents to thereby obtain Compound 83(yellow solid, 2.2 g, 7%). The obtained yellow solid was identified byESI-LCMS and ¹H-NMR as Compound 83.

ESI-LCMS: [M]⁺: C₁₁₄H₇₈B₂N₆. 1552.4437.

¹H-NMR (400 MHz, CDCl₃): 10.17 (s, 1H), 9.33 (d, 2H), 8.22 (d, 2H), 8.13(d, 4H), 7.41 (m, 23H), 7.24 (m, 20H), 7.08 (m, 18H), 6.91 (s, 1H), 6.43(s, 4H).

Synthesis Example 11: Synthesis of Compound 85

Synthesis of Intermediate Compound 85-a

In an argon atmosphere, 3,5-dibromo-chlorobenzene (35 g, 111 mmol),N-phenyl-[1,1′:3′,1″-terphenyl]-2′-amine (36 g, 111 mmol), sodiumtert-butoxide (32 g, 333 mmol), tris-tert-butyl phosphine (5.1 ml, 11mmol), and Pd₂dba₃ (5.1 g, 5.6 mmol) were added to a 2 L flask anddissolved in 1 L of o-xylene, and the reaction solution was stirred attemperature of 100° C. for 12 hours. After cooling, water (1 L) andethylacetate (300 ml) were added thereto for extraction and collectionof an organic layer, and was dried using MgSO₄ and filtered. Thefiltered solution was placed under reduced pressure to remove solventtherefrom, and the obtained solid was purified and separated by columnchromatography using silica gel using CH₂Cl₂ and hexane as developmentsolvents to thereby obtain Intermediate compound 85-a (white solid, 55g, 67%). The obtained white solid was identified by ESI-LCMS asIntermediate compound 85-a.

ESI-LCMS: [M]⁺: C₅₄H₃₉N₂Cl. 750.2812.

Synthesis of Intermediate Compound 85-b

In an argon atmosphere, Compound 85-a (55 g, 73 mmol), aniline (7 g, 111mmol), sodium tert-butoxide (21 g, 219 mmol), tris-tert-butyl phosphine(3.3 ml, 7.2 mmol), and Pd₂dba₃ (3.3 g, 3.6 mmol) were added to a 2 Lflask and dissolved in 700 ml of o-xylene, and the reaction solution wasstirred at a temperature of 140° C. for 12 hours. After cooling, water(1 L) and ethylacetate (300 ml) were added thereto for extraction andcollection of an organic layer, and was dried using MgSO₄ and filtered.The filtered solution was placed under reduced pressure to removesolvent therefrom, and the obtained solid was purified and separated bycolumn chromatography using silica gel using CH₂Cl₂ and hexane asdevelopment solvents to thereby obtain Intermediate compound 85-b (whitesolid, 38 g, 64%). The obtained white solid was identified by ESI-LCMSas Intermediate compound 85-b.

ESI-LCMS: [M]⁺: C₆₀H₄₅N₃. 807.3515.

Synthesis of Intermediate Compound 85-c

In an argon atmosphere, Compound 85-b (30 g, 37 mmol), Compound 55-b (30g, 37 mmol), sodium tert-butoxide (10 g, 111 mmol), tris-tert-butylphosphine (1.7 ml, 3.6 mmol), and Pd₂dba₃ (1.7 g, 1.8 mmol) were addedto a 2 L flask and dissolved in 400 ml of o-xylene, and the reactionsolution was stirred at a temperature of 140° C. for 12 hours. Aftercooling, water (1 L) and ethylacetate (300 ml) were added thereto forextraction and collection of an organic layer, and was dried using MgSO₄and filtered. The filtered solution was placed under reduced pressure toremove solvent therefrom, and the obtained solid was purified andseparated by column chromatography using silica gel using CH₂Cl₂ andhexane as development solvents to thereby obtain Intermediate compound85-c (white solid, 24 g, 48%). The obtained white solid was identifiedby ESI-LCMS as Intermediate compound 85-c.

ESI-LCMS: [M]⁺: C₁₁₄H₈₄N₆. 1536.6123.

Synthesis of Compound 85

In an argon atmosphere, Compound 85-c (24 g, 15 mmol) was added to a 1 Lflask, dissolved in 500 ml of o-dichlorobenzene, and cooled to 0° C. inan ice water vessel. Boron tribromide (5 eq.) was slowly added dropwiseto the reaction solution, and the temperature was slowly raised to roomtemperature. The reaction solution was heated to a temperature of 180°C. and stirred for 12 hours. After cooling, triethylamine (5 ml) wasslowly added dropwise thereto to terminate the reaction and solvent wasremoved therefrom under reduced pressure. The obtained solid was washedwith MeOH and was purified and separated by column chromatography usingsilica gel using CH₂Cl₂ and hexane as development solvents to therebyobtain Compound 85 (yellow solid, 1.8 g, 8%). The obtained yellow solidwas identified by ESI-LCMS and ¹H-NMR as Compound 85.

ESI-LCMS: [M]⁺: C₁₁₄H₇₈B₂N₆. 1552.6512.

¹H-NMR (400 MHz, CDCl₃): 10.22 (s, 1H), 9.27 (d, 2H), 8.25 (d, 6H), 7.36(m, 21H), 7.21 (m, 14H), 7.02 (m, 29H), 6.88 (s, 1H), 6.47 (s, 4H).

Synthesis Example 12: Synthesis of Compound 97

Synthesis of Intermediate Compound 97-a

In an argon atmosphere, 1,3-dibromo-5-chlorobenzene (30 g, 111 mmol),4′-(tert-butyl)-N-phenyl-[1,1′-biphenyl]-2-amine (67 g, 222 mmol),sodium tert-butoxide (32 g, 333 mmol), tris-tert-butyl phosphine (5 ml,11 mmol), and Pd₂dba₃ (5.1 g, 5.6 mmol) were added to a 2 L flask anddissolved in 1 L of o-xylene, and the reaction solution was stirred attemperature of 100° C. for 12 hours. After cooling, water (1 L) andethylacetate (300 ml) were added thereto for extraction and collectionof an organic layer, and was dried using MgSO₄ and filtered. Thefiltered solution was placed under reduced pressure to remove solventtherefrom, and the obtained solid was purified and separated by columnchromatography using silica gel using CH₂Cl₂ and hexane as developmentsolvents to thereby obtain Intermediate compound 97-a (white solid, 46g, 59%). The obtained white solid was identified by ESI-LCMS asIntermediate compound 97-a.

ESI-LCMS: [M]⁺: C₅₀H₄₇N₂Cl. 710.3336.

Synthesis of Intermediate Compound 97-b

In an argon atmosphere, Compound 97-a (45 g, 63 mmol), aniline (6.1 g,63 mmol), sodium tert-butoxide (18 g, 190 mmol), tris-tert-butylphosphine (3 ml, 6.4 mmol), and Pd₂dba₃ (2.9 g, 3.2 mmol) were added toa 2 L flask and dissolved in 600 ml of o-xylene, and the reactionsolution was stirred at a temperature of 140° C. for 12 hours. Aftercooling, water (1 L) and ethylacetate (300 ml) were added thereto forextraction and collection of an organic layer, and was dried using MgSO₄and filtered. The filtered solution was placed under reduced pressure toremove solvent therefrom, and the obtained solid was purified andseparated by column chromatography using silica gel using CH₂Cl₂ andhexane as development solvents to thereby obtain Intermediate compound97-b (white solid, 35 g, 72%). The obtained white solid was identifiedby ESI-LCMS as Intermediate compound 97-b.

ESI-LCMS: [M]⁺: C₅₆H₅₃N₃. 767.4321.

Synthesis of Intermediate Compound 97-c

In an argon atmosphere, Compound 97-a (30 g, 42 mmol),[1,1′:3′,1″-terphenyl]-2′-amine (10 g, 42 mmol), sodium tert-butoxide(12 g, 126 mmol), tris-tert-butyl phosphine (2 ml, 4.2 mmol), andPd2dba₃ (1.9 g, 2.1 mmol) were added to a 2 L flask and dissolved in 400ml of o-xylene, and the reaction solution was stirred at a temperatureof 140° C. for 12 hours. After cooling, water (1 L) and ethylacetate(300 ml) were added thereto for extraction and collection of an organiclayer, and was dried using MgSO₄ and filtered. The filtered solution wasplaced under reduced pressure to remove solvent therefrom, and theobtained solid was purified and separated by column chromatography usingsilica gel using CH₂Cl₂ and hexane as development solvents to therebyobtain Intermediate compound 97-c (white solid, 20 g, 54%). The obtainedwhite solid was identified by ESI-LCMS as Intermediate compound 97-c.

ESI-LCMS: [M]⁺: C₆₇H₅₉N₃. 905.4731.

Synthesis of Intermediate Compound 97-d

In an argon atmosphere, Compound 97-c (20 g, 22 mmol),3-bromo-iodobenzene (10 g, 22 mmol), sodium tert-butoxide (6.4 g, 66mmol), tris-tert-butyl phosphine (1 ml, 2.2 mmol), and Pd₂dba₃ (1.0 g,1.1 mmol) were added to a 1 L flask and dissolved in 250 ml of o-xylene,and the reaction solution was stirred at a temperature of 100° C. for 12hours. After cooling, water (1 L) and ethylacetate (300 ml) were addedthereto for extraction and collection of an organic layer, and was driedusing MgSO₄ and filtered. The filtered solution was placed under reducedpressure to remove solvent therefrom, and the obtained solid waspurified and separated by column chromatography using silica gel usingCH₂Cl₂ and hexane as development solvents to thereby obtain Intermediatecompound 97-d (white solid, 16 g, 71%). The obtained white solid wasidentified by ESI-LCMS as Intermediate compound 97-d.

ESI-LCMS: [M]⁺: C₇₄H₆₄N₃Br. 1073.2917.

Synthesis of Intermediate Compound 97-e

In an argon atmosphere, Compound 97-d (15 g, 14 mmol), Compound 97-b(9.2 g, 14 mmol), sodium tert-butoxide (4 g, 42 mmol), tris-tert-butylphosphine (0.6 ml, 1.4 mmol), and Pd₂dba₃ (0.6 g, 0.7 mmol) were addedto a 1 L flask and dissolved in 150 ml of o-xylene, and the reactionsolution was stirred at a temperature of 100° C. for 12 hours. Aftercooling, water (1 L) and ethylacetate (300 ml) were added thereto forextraction and collection of an organic layer, and was dried using MgSO₄and filtered. The filtered solution was placed under reduced pressure toremove solvent therefrom, and the obtained solid was purified andseparated by column chromatography using silica gel using CH₂Cl₂ andhexane as development solvents to thereby obtain Intermediate compound97-e (white solid, 16 g, 66%). The obtained white solid was identifiedby ESI-LCMS as Intermediate compound 97-e.

ESI-LCMS: [M]⁺: C₁₃₀H₁₁₆N₆. 1760.9331.

Synthesis of Compound 97

In an argon atmosphere, Compound 97-e (15 g, 8.5 mmol) was added to a 1L flask, dissolved in 500 ml of o-dichlorobenzene, and cooled to 0° C.in an ice water vessel. Boron tribromide (5 eq.) was slowly addeddropwise to the reaction solution, and the temperature was slowly raisedto room temperature. The reaction solution was heated to a temperatureof 180° C. and stirred for 12 hours. After cooling, triethylamine (5 ml)was slowly added dropwise thereto to terminate the reaction and solventwas removed therefrom under reduced pressure. The obtained solid waswashed with MeOH and was purified and separated by column chromatographyusing silica gel using CH₂Cl₂ and hexane as development solvents tothereby obtain Compound 97 (yellow solid, 1.2 g, 8%). The obtainedyellow solid was identified by ESI-LCMS and ¹H-NMR as Compound 97.

ESI-LCMS: [M]⁺: C₁₃₀H₁₁₀B₂N₆. 1776.8997.

¹H-NMR (400 MHz, CDCl₃): 10.34 (s, 1H), 9.41 (d, 2H), 8.12 (d, 4H), 7.44(m, 32H), 7.24 (m, 21H), 7.00 (m, 9H), 6.84 (s, 1H), 6.52 (s, 4H), 1.33(s, 36H).

Synthesis Example 13: Synthesis of Compound 101

Synthesis of Intermediate Compound 101-a

In an argon atmosphere, Compound 83-b (30 g, 46 mmol),3-bromo-iodobenzene (13 g, 46 mmol), sodium tert-butoxide (13 g, 138mmol), tris-tert-butyl phosphine (2.2 ml, 4.6 mmol), and Pd₂dba₃ (2.1 g,2.3 mmol) were added to a 2 L flask and dissolved in 500 ml of o-xylene,and the reaction solution was stirred at a temperature of 140° C. for 12hours. After cooling, water (1 L) and ethylacetate (300 ml) were addedthereto for extraction and collection of an organic layer, and was driedusing MgSO₄ and filtered. The filtered solution was placed under reducedpressure to remove solvent therefrom, and the obtained solid waspurified and separated by column chromatography using silica gel usingCH₂Cl₂ and hexane as development solvents to thereby obtain Intermediatecompound 101-a (white solid, 21 g, 56%). The obtained white solid wasidentified by ESI-LCMS as Intermediate compound 101-a.

ESI-LCMS: [M]⁺: C₅₄H₄₀N₃Br. 809.2434.

Synthesis of Intermediate Compound 101-b

In an argon atmosphere,5-chloro-N1,N1,N3,N3-tetraphenylbenzene-1,3-diamine (30 g, 67 mmol),4,4″-di-tert-butyl-[1,1′:3′,1″-terphenyl]-2′-amine (24 g, 67 mmol),sodium tert-butoxide (19 g, 201 mmol), tris-tert-butyl phosphine (6 ml,6.8 mmol), and Pd₂dba₃ (3 g, 3.4 mmol) were added to a 2 L flask anddissolved in 500 ml of o-xylene, and the reaction solution was stirredat a temperature of 140° C. for 12 hours. After cooling, water (1 L) andethylacetate (300 ml) were added thereto for extraction and collectionof an organic layer, and was dried using MgSO₄ and filtered. Thefiltered solution was placed under reduced pressure to remove solventtherefrom, and the obtained solid was purified and separated by columnchromatography using silica gel using CH₂Cl₂ and hexane as developmentsolvents to thereby obtain Intermediate compound 101-b (white solid, 37g, 72%). The obtained white solid was identified by ESI-LCMS asIntermediate compound 101-b.

ESI-LCMS: [M]⁺: C₅₆H₅₆N₃. 767.4119.

Synthesis of Intermediate Compound 101-c

In an argon atmosphere, Compound 101-a (20 g, 25 mmol), Compound 101-b(19 g, 25 mmol), sodium tert-butoxide (7.2 g, 75 mmol), tris-tert-butylphosphine (1.2 ml, 2.6 mmol), and Pd₂dba₃ (1.1 g, 1.3 mmol) were addedto a 2 L flask and dissolved in 250 ml of o-xylene, and the reactionsolution was stirred at a temperature of 140° C. for 12 hours. Aftercooling, water (1 L) and ethylacetate (300 ml) were added thereto forextraction and collection of an organic layer, and was dried using MgSO₄and filtered. The filtered solution was placed under reduced pressure toremove solvent therefrom, and the obtained solid was purified andseparated by column chromatography using silica gel using CH₂Cl₂ andhexane as development solvents to thereby obtain Intermediate compound101-c (white solid, 23.5 g, 65%). The obtained white solid wasidentified by ESI-LCMS as Intermediate compound 101-c.

ESI-LCMS: [M]⁺: C₁₁₀H₅₂N₆. 1497.2331.

Synthesis of Compound 101

In an argon atmosphere, Compound 101-c (20 g, 8.5 mmol) was added to a 1L flask, dissolved in 500 ml of o-dichlorobenzene, and cooled to 0° C.in an ice water vessel. Boron tribromide (5 eq.) was slowly addeddropwise to the reaction solution, and the temperature was slowly raisedto room temperature. The reaction solution was heated to a temperatureof 180° C. and stirred for 12 hours. After cooling, triethylamine (5 ml)was slowly added dropwise thereto to terminate the reaction and solventwas removed therefrom under reduced pressure. The obtained solid waswashed with MeOH and purified and separated by column chromatographyusing silica gel using CH₂Cl₂ and hexane as development solvents tothereby obtain Compound 101 (yellow solid, 1 g, 10%). The obtainedyellow solid was identified by ESI-LCMS and ¹H-NMR as Compound 101.

ESI-LCMS: [M]⁺: C₁₁₀H₈₆B₂N₆. 1512.7171.

¹H-NMR (400 MHz, CDCl₃): 10.29 (s, 1H), 9.23 (d, 2H), 8.21 (d, 2H), 8.10(d, 2H), 7.39 (m, 15H), 7.24 (m, 10H), 7.08 (m, 14H), 7.00 (m, 5H), 6.81(s, 1H), 6.47 (s, 4H), 1.37 (s, 18H).

Proton nuclear magnetic resonance ¹H NMR and Matrix-Assisted LaserDesorption/Ionization Time-of-Flight mass-spectrometer (MALDI-TOF MS) ofthe compounds synthesized according to Synthesis Examples 1 to 13 areshown in Table 1.

Synthesis methods for compounds other than the compounds shown inSynthesis Examples 1 to 13 may be easily recognized by those skilled inthe technical field by referring to the synthesis paths and sourcematerials described above.

TABLE 1 Compound ¹H NMR (CDCl₃, 400 MHz) ESI-MS [M⁺] 1 10.46 (s, 1H),9.94 (d, 2H), 9.31 (d, 1H), 8.37 (d, 1H), 8.20 (d, 2H), 7.39 (m, 3H),7.24 (m, 18H), 7.03 (m, 27H), 6.83 (s, 1H), 6.49 (m, 4H). 1173.4936. 1710.52 (s, 1H), 9.83 (d, 2H), 9.41 (d, 2H), 7.39 (t, 1H), 7.31 (m, 2H),7.24 (m, 16H), 7.08 (m, 21H), 7.01 (t, 2H), 6.83 (s, 1H), 6.77 (d, 2H),6.49 (m, 4H). 1362.6617. 31 10.26 (s, 1H), 9.65 (d, 2H), 9.41 (d, 2H),9.31 (d, 2H), 8.37 (d, 3H), 8.20 (m, 1H), 7.39 (m, 10H), 7.24 (m, 12H),7.08 (m, 24H), 6.77 (s, 1H), 7.01 (t, 2H), 6.49 (s, 2H). 1395.4434. 3710.31 (s, 1H), 9.42 (d, 2H), 8.45 (d, 2H), 8.37 (d, 2H), 7.83 (t, 1H),7.38 (m, 4H), 7.24 (m, 12H), 7.08 (m, 12H), 6.90 (m, 9H), 6.83 (t, 1H),6.52 (d, 4H). 1176.0157. 41 10.78 (s, 1H), 9.87 (d, 2H), 9.31 (d, 4H),8.37 (d, 4H), 7.39 (m, 12H), 7.21 (m, 8H), 7.04 (m, 24H), 6.65 (s, 1H),6.50 (d, 4H). 1254.4644. 50 10.56 (s, 1H), 9.76 (d, 2H), 9.41 (d, 4H),8.37 (d, 4H), 7.41 (m, 6H), 7.27 (m, 8H), 7.12 (m, 14H), 6.88 (s, 2H).1136.3336. 55 10.43 (s, 1H), 9.58 (d, 2H), 9.31 (d, 2H), 8.37 (d, 2H),8.20 (d, 2H), 7.76 (s, 1H), 7.41 (m, 7H), 7.25 (m, 13H), 7.12 (m, 17H),6.57 (s, 1H), 6.49 (s, 2H). 1343.5001. 57 10.59 (s, 1H), 9.68 (d, 2H),9.31 (d, 2H), 8.37 (d, 2H), 8.20 (d, 2H), 7.76 (s, 1H), 7.43 (m, 9H),7.27 (m, 21H), 7.12 (m, 17H), 7.03 (m, 7H), 6.83 (s, 1H), 6.49 (s, 4H).1402.5554. 82 10.36 (s, 1H), 9.22 (d, 2H), 8.20 (d, 2H), 8.10 (d, 3H),7.43 (m, 13H), 7.24 (m, 16H), 7.12 (m, 20H), 7.01 (m, 7H), 6.87 (s, 1H),6.52 (s, 4H). 1476.6551. 83 10.17 (s, 1H), 9.33 (d, 2H), 8.22 (d, 2H),8.13 (d, 4H), 7.41 (m, 23H), 7.24 (m, 20H), 7.08 (m, 18H), 6.91 (s, 1H),6.43 (s, 4H). 1552.4437. 85 10.22 (s, 1H), 9.27 (d, 2H), 8.25 (d, 6H),7.36 (m, 21H), 7.21 (m, 14H), 7.02 (m, 29H), 6.88 (s, 1H), 6.47 (s, 4H).1552.6512. 97 10.34 (s, 1H), 9.41 (d, 2H), 8.12 (d, 4H), 7.44 (m, 32H),7.24 (m, 21H), 7.00 (m, 9H), 6.84 (s, 1H), 6.52 (s, 4H), 1.33 (s, 36H).1776.8997. 101 10.29 (s, 1H), 9.23 (d, 2H), 8.21 (d, 2H), 8.10 (d, 2H),7.39 (m, 15H), 7.24 (m, 10H), 7.08 (m, 14H), 7.00 (m, 5H), 6.81 (s, 1H),6.47 (s, 4H), 1.37 (s, 18H). 1512.7171.

Example 1

As an anode, a glass substrate (product of Corning Inc. of Corning, N.Y.(hereinafter “Corning Inc.”)) with a 15 Ω/cm² (1,200 Å) ITO electrodeformed thereon was cut to a size of 50 mm×50 mm×0.7 mm, sonicated withisopropyl alcohol and pure water each for 5 minutes, and then cleaned byexposure to ultraviolet rays and ozone for 30 minutes. Then, theresultant structure was mounted on a vacuum deposition apparatus.

The compound NPD was deposited on the anode to form a hole injectionlayer having a thickness of 300 Å, the compound HT6 was deposited on thehole injection layer to form a hole transport layer having a thicknessof 200 Å, and the compound CzSi was deposited on the hole transportlayer to form an emission auxiliary layer having a thickness of 100 Å.

The compound mCP (host) and Compound 1 (dopant) were co-deposited to aweight ratio of 99:1 on the emission auxiliary layer to form an emissionlayer having a thickness of 200 Å.

Subsequently, the compound TSPO1 was deposited on the emission layer toform a hole blocking layer having a thickness of 200 Å, the compoundTPBi was deposited on the hole blocking layer to form an electrontransport layer having a thickness of 300 Å, the compound lithiumfluoride (LiF) was deposited on the electron transport layer to form anelectron injection layer having a thickness of 10 Å, the element Al wasdeposited on the electron injection layer to form a cathode having athickness of 3,000 Å, and the compound HT28 was deposited on theelectrode to form a capping layer having a thickness of 700 Å, therebycompleting the manufacture of a light-emitting device.

Examples 2 to 13 and Comparative Examples 1 to 3

Organic light-emitting devices were manufactured in the same manner asin Example 1, except that, in forming an emission layer, for use as adopant, corresponding compounds shown in Table 1 were used instead ofCompound 1.

Example 14

As an anode, a glass substrate (product of Corning Inc.) with a 15 Ω/cm²(1,200 Å) ITO electrode formed thereon was cut to a size of 50 mm×50mm×0.7 mm, sonicated with isopropyl alcohol and pure water each for 5minutes, and then cleaned by exposure to ultraviolet rays and ozone for30 minutes. Then, the resultant structure was mounted on a vacuumdeposition apparatus.

The compound NPD was deposited on the anode to form a hole injectionlayer having a thickness of 300 Å, the compound HT45 was deposited onthe hole injection layer to form a hole transport layer having athickness of 200 Å, and the compound CzSi was deposited on the holetransport layer to form an emission auxiliary layer having a thicknessof 100 Å.

The compounds H39 and H37 (weight ratio of 5:5) used in an amount of 84wt. % as a mixed host, the compound PD26 used in an amount of 15 wt. %as a metal phosphorescent dopant, and Compound 55 used in an amount of 1wt. % as a dopant were co-deposited on the emission auxiliary layer toform an emission layer having a thickness of 200 Å.

Subsequently, the compound TSPO1 was deposited on the emission layer toform a hole blocking layer having a thickness of 200 Å, the compoundTPBI was deposited on the hole blocking layer to form an electrontransport layer having a thickness of 300 Å, the compound LiF wasdeposited on the electron transport layer to form an electron injectionlayer having a thickness of 10 Å, the element Al was deposited on theelectron injection layer to form a cathode having a thickness of 3,000Å, and the compound HT28 was deposited on the electrode to form acapping layer having a thickness of 700 Å, thereby completing themanufacture of a light-emitting device.

Examples 15 to 21 and Comparative Examples 4 to 6

Light-emitting devices were manufactured in the same manner as inExample 14, except that, for use as a hole transport layer material, ahost, and a dopant, corresponding compounds shown in Table 2 were used.

Example 22

As an anode, a glass substrate (product of Corning Inc.) with a 15 Ω/cm²(1,200 Å) ITO electrode formed thereon was cut to a size of 50 mm×50mm×0.7 mm, sonicated with isopropyl alcohol and pure water each for 5minutes, and then cleaned by exposure to ultraviolet rays and ozone for30 minutes. Then, the resultant structure was mounted on a vacuumdeposition apparatus.

The compound NPD was deposited on the anode to form a hole injectionlayer having a thickness of 300 Å, the compound HT45 was deposited onthe hole injection layer to form a hole transport layer having athickness of 200 Å, and the compound CzSi was deposited on the holetransport layer to form an emission auxiliary layer having a thicknessof 100 Å.

The compounds H39 and H37 (weight ratio of 5:5) used in an amount of 84wt. % as a mixed host, the compound PD26 used in an amount of 15 wt. %as a metal phosphorescent dopant, and Compound 17 used in an amount of 1wt. % as a dopant were co-deposited on the emission auxiliary layer toform an emission layer having a thickness of 200 Å.

Subsequently, the compound TSPO1 was deposited on the emission layer toform a hole blocking layer having a thickness of 200 Å, the compound ET1was deposited on the hole blocking layer to form an electron transportlayer having a thickness of 300 Å, the compound LiF was deposited on theelectron transport layer to form an electron injection layer having athickness of 10 Å, the element Al was deposited on the electroninjection layer to form a cathode having a thickness of 3,000 Å, and thecompound HT28 was deposited on the electrode to form a capping layerhaving a thickness of 700 Å, thereby completing the manufacture of alight-emitting device.

Examples 23 to 29 and Comparative Examples 7 and 8

Light-emitting devices were manufactured in the same manner as inExample 22, except that, for use as a hole transport layer material, ahost, and a dopant, corresponding compounds shown in Table 4 were used.

Evaluation Example 2

The driving voltage in volt (V) at 1,000 in candela per square meter(cd/A or cd/m²), emission efficiency (cd/A), and emission color of theorganic light-emitting devices manufactured according to Examples 1 to29 and Comparative Examples 1 to 8 were measured by using a source meter(sold under the trade designation Keithley MU 236, by Tektronix, Inc.,of Beaverton, Oreg.) and a luminance meter sold under the tradedesignation PR650 by Photo Research Inc. of Los Angeles, Calif. The(T₉₅) lifespan is the time it takes to achieve 95% of the initialluminance measured in hour at 100 milliamp per centimeter squared.

Results thereof are shown in Tables 2 to 4.

TABLE 2 Driving Emission voltage efficiency Emission Lifespan (T₉₅)/ No.Dopant (V) (cd/A) wavelength relative lifespan Example 1  1 4.1 24.7 464 75/1.50 Example 2 17 3.9 25.4 463  95/1.90 Example 3 31 3.8 27.6 455 62/1.24 Example 4 37 3.6 24.1 453  55/1.10 Example 5 41 3.8 25.5 455 66/1.32 Example 6 50 4.0 27.8 452  53/1.06 Example 7 55 4.1 26.8 460102/2.04 Example 8 57 3.9 25.8 463 110/2.20 Example 9 82 4.5 23.7 462 76/1.52 Example 10 83 4.6 22.6 462  93/1.86 Example 11 85 4.8 23.0 461105/2.10 Example 12 97 4.7 21.9 462  95/1.90 Example 13 101  4.8 22.1463  75/1.50 Comparative A 5.2 15.7 462 25/0.5 Example 1 Comparative B4.8 21.2 466  50/1.00 Example 2 Comparative C 4.5 10.7 445 10/0.2Example 3

TABLE 3 Metal Lifespan Hole phos- Driving Emission Emission (T₉₅)/transport phorescent voltage efficiency wave- relative No. layer Hostdopant Dopant (V) (cd/A) length lifespan Example 14 HT45 H39 + H37 PD2655 3.8 28.8 460 2.38 Example 15 HT45 H39 + H37 PD26 57 3.6 27.0 462 2.56Example 16 HT45 H39 + H37 PD26 85 4.4 25.4 461 2.17 Example 17 HT45H39 + H37 PD26 97 4.2 22.8 462 2.13 Example 18 HT46 H39 + H37 PD26  13.7 27.9 459 1.98 Example 19 HT46 H39 + H37 PD26 31 3.5 26.8 463 2.16Example 20 HT46 H39 + H37 PD26 83 4.3 24.8 462 2.01 Example 21 HT46H39 + H37 PD26 85 4.3 23   463 2.00 Comparative HT45 H39 + H37 PD26 A4.9 17.7 461 0.58 Example 4 Comparative HT45 H39 + H37 PD26 B 4.5 23.5465 1.40 Example 5 Comparative HT45 H39 + H37 PD26 C 4.3 12.5 444 0.43Example 6

TABLE 4 Metal Lifespan Hole Electron phos- Driving Emission Emission(T₉₅)/ transport transport phorescent voltage efficiency wave- relativeNo. layer Host layer dopant Dopant (V) (cd/A) length lifespan Example 22HT45 H39 + H37 ET1 PD26 17 3.8 26.8 463 1.68 Example 23 HT45 H39 + H37ET1 PD26 37 3.6 25.5 454 1.09 Example 24 HT45 H39 + H37 ET1 PD26 41 3.825.1 455 1.24 Example 25 HT45 H39 + H37 ET1 PD26 101  4.5 23.8 463 1.36Example 26 HT45 H39 + H37 ET1 + Alq₃ PD26 31 3.6 26.5 455 1.48 Example27 HT45 H39 + H37 ET1 + Alq₃ PD26 41 3.7 24.8 455 1.73 Example 28 HT45H39 + H37 ET1 + Alq₃ PD26 83 4.5 24.1 462 2.21 Example 29 HT45 H39 + H37ET1 + Alq₃ PD26 85 4.7 25.0 461 2.68 Comparative HT45 H39 + H37 ET1 PD26C 4.5 11.9 445 0.39 Example 7 Comparative HT45 H39 + H37 ET1 + Alq₃ PD26C 4.7 10.6 444 0.61 Example 8

Table 2 shows that the light-emitting devices of Examples 1 to 13 emitblue light having a wavelength range of 450 nm to 470 nm and havesignificantly and unexpectedly improved driving voltage, emissionefficiency, and lifespan characteristics as compared with thelight-emitting devices of Comparative Examples 1 to 3.

Table 3 shows that the light-emitting devices of Examples 14 to 21 emitblue light having a wavelength range of 450 nm to 470 nm and havesignificantly and unexpectedly improved characterisitics including lowerdriving voltage, higher emission efficiency, and longer lifespan ascompared with the light-emitting devices of Comparative Examples 4 to 6.

Table 4 shows that the light-emitting devices of Examples 22 to 29 emitblue light having a wavelength range of 450 nm to 470 nm and havesignificantly and unexpectedly improved characteristics including lowerdriving voltage, higher emission efficiency, and longer lifespan ascompared with the light-emitting devices of Comparative Examples 7 and8.

Although not wanting to be bound by theory, because the light-emittingdevice includes a heterocyclic compound represented by Formula 1, thelight-emitting device may have low driving voltage, high emissionefficiency, and high external quantum efficiency, and high-qualityelectronic apparatuses may be manufactured.

Although certain embodiments and implementations have been describedherein, other embodiments and modifications will be apparent from thisdescription. Accordingly, the inventive concepts are not limited to suchembodiments, but rather to the broader scope of the appended claims andvarious obvious modifications and equivalent arrangements as would beapparent to a person of ordinary skill in the art.

What is claimed is:
 1. A light-emitting device including: a firstelectrode; a second electrode facing the first electrode; and aninterlayer between the first electrode and the second electrode andincluding an emission layer, wherein the interlayer comprises aheterocyclic compound of Formula 1:

wherein, in Formulae 1, 1-1, and 1-2, A₁ is a group of Formula 1-1, isB₁ is a group of Formula 1-2, n1 is an integer from 1 to 10, CY₁ to CY₄are each, independently from one another, a C₅-C₃₀ carbocyclic group ora C₁-C₃₀ heterocyclic group, Y₁ and Y₂ are each, independently from oneanother, B, P(═O), or P(═S), X₁ is O, S, Se, Te, N(Ar₁), Al(Ar₁), orP(Ar₁), X₂ is O, S, Se, Te, N(Ar₂), Al(Ar₂), or P(Ar₂), X₃ is O, S, Se,Te, N(Ar₃), Al(Ar₃), or P(Ar₃), X₄ is O, S, Se, Te, N(Ar₄), Al(Ar₄), orP(Ar₄), Ar₁ to Ar₁₀ are each, independently from one another, a bindingsite to B₁ in Formula 1, hydrogen, deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, a C₁-C₆₀ alkyl groupunsubstituted or substituted with at least one R_(10a), a C₂-C₆₀ alkenylgroup unsubstituted or substituted with at least one R_(10a), a C₂-C₆₀alkynyl group unsubstituted or substituted with at least one R_(10a), aC₁-C₆₀ alkoxy group unsubstituted or substituted with at least oneR_(10a), a C₃-C₆₀ carbocyclic group unsubstituted or substituted with atleast one R_(10a), a C₁-C₆₀ heterocyclic group unsubstituted orsubstituted with at least one R_(10a), a C₆-C₆₀ aryloxy groupunsubstituted or substituted with at least one R_(10a), a C₆-C₆₀arylthio group unsubstituted or substituted with at least one R_(10a),—C(Q₁)(Q₂)(Q₃), —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁),—S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂), at least one of Ar₁ to Ar₁₀ are abinding site to B₁ in Formula 1, T₁₁ is a C₃-C₆₀ carbocyclic groupunsubstituted or substituted with at least one R_(10a) or a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least oneR_(10a), X₁₁ is N or C(R₁₁), X₁₂ is N or C(R₁₂), X₁₃ is N or C(R₁₃), andX₁₄ is N or C(R₁₄), R₁ to R₄ and R₁₁ to R₁₄ are each, independently fromone another, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, a C₁-C₆₀ alkyl group unsubstituted orsubstituted with at least one R_(10a), a C₂-C₆₀ alkenyl groupunsubstituted or substituted with at least one R_(10a), a C₂-C₆₀ alkynylgroup unsubstituted or substituted with at least one R_(10a), a C₁-C₆₀alkoxy group unsubstituted or substituted with at least one R_(10a), aC₃-C₆₀ carbocyclic group unsubstituted or substituted with at least oneR_(10a), a C₁-C₆₀ heterocyclic group unsubstituted or substituted withat least one R_(10a), a C₆-C₆₀ aryloxy group unsubstituted orsubstituted with at least one R_(10a), a C₆-C₆₀ arylthio groupunsubstituted or substituted with at least one R_(10a), —C(Q₁)(Q₂)(Q₃),—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), or—P(═O)(Q₁)(Q₂), a1 to a4 are each, independently from one another, aninteger from 0 to 10, when a1 is an integer of 2 or more, two or more ofR₁(s) are optionally linked to each other to form a C₃-C₆₀ carbocyclicgroup unsubstituted or substituted with at least one R_(10a) or a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least oneR_(10a), when a2 is an integer of 2 or more, two or more of R₂(s) areoptionally linked to each other to form a C₃-C₆₀ carbocyclic groupunsubstituted or substituted with at least one R_(10a) or a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least oneR_(10a), when a3 is an integer of 2 or more, two or more of R₃(s) areoptionally linked to each other to form a C₃-C₆₀ carbocyclic groupunsubstituted or substituted with at least one R_(10a) or a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least oneR_(10a), when a4 is an integer of 2 or more, two or more of R₄(s) areoptionally linked to each other to form a C₃-C₆₀ carbocyclic groupunsubstituted or substituted with at least one R_(10a) or a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least oneR_(10a), two or more neighboring groups of R₁₁ to R₁₄ are optionallylinked to each other to form a C₃-C₆₀ carbocyclic group unsubstituted orsubstituted with at least one R_(10a) or a C₁-C₆₀ heterocyclic groupunsubstituted or substituted with at least one R_(10a), * in Formula 1-2is a binding site to A₁ in Formula 1, and R_(10a) is: deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group; aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, or aC₁-C₆₀ alkoxy group each, independently from one another, unsubstitutedor substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, a C₃-C₆₀ carbocyclic group, a C₁-C₆₀heterocyclic group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), —P(═O)(Q₁₁)(Q₁₂), or any combination thereof; a C₃-C₆₀carbocyclic group, a C₁-C₆₀ heterocyclic group, a C₆-C₆₀ aryloxy group,or a C₆-C₆₀ arylthio group each, independently from one another,unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, aC₃-C₆₀ carbocyclic group, a C₁-C₆₀ heterocyclic group, a C₆-C₆₀ aryloxygroup, a C₆-C₆₀ arylthio group, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂),—B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), —P(═O)(Q₂₁)(Q₂₂), or anycombination thereof; or —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂),—C(═O)(Q₃₁), —S(═O)₂(Q₃₁), or —P(═O)(Q₃₁)(Q₃₂), wherein Q₁ to Q₃, Q₁₁ toQ₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ are each, independently from oneanother: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; acyano group; a nitro group; a C₁-C₆₀ alkyl group; a C₂-C₆₀ alkenylgroup; a C₂-C₆₀ alkynyl group; a C₁-C₆₀ alkoxy group; a C₃-C₆₀carbocyclic group; or a C₁-C₆₀ heterocyclic group each, independentlyfrom one another, unsubstituted or substituted with deuterium, —F, acyano group, a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkoxy group, a phenylgroup, a biphenyl group, or any combination thereof.
 2. Thelight-emitting device of claim 1, wherein the heterocyclic compound ofFormula 1 is included in the emission layer.
 3. The light-emittingdevice of claim 2, wherein an organometallic compound of Formula 401 isfurther included in the emission layer:

wherein, in Formulae 401 and 402, M is a transition metal, L₄₀₁ is aligand of Formula 402, and xc1 is 1, 2, or 3, wherein when xc1 is 2 or3, two or more of L₄₀₁(s) are identical to or different from each other,L₄₀₂ is an organic ligand, xc2 is 0, 1, 2, 3, or 4, and when xc2 is 2, 3or 4, two or more of L₄₀₂(s) are identical to or different from eachother, X₄₀₁ and X₄₀₂ are each, independently from one another, nitrogenor carbon, ring A₄₀₁ and ring A₄₀₂ are each, independently from oneanother, a C₃-C₆₀ carbocyclic group or a C₁-C₆₀ heterocyclic group, T₄₀₁is a single bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—N(Q₄₁₁)-*′,*—C(Q₄₁₁)(Q₄₁₂)-*′, *—C(Q₄₁₁)=C(Q₄₁₂)-*′, *—C(Q₄₁₁)=*′, or *═C═*′, X₄₀₃and X₄₀₄ are each, independently from one another, a chemical bond, O,S, N(Q₄₁₃), B(Q₄₁₃), P(Q₄₁₃), C(Q₄₁₃)(Q₄₁₄), or Si(Q₄₁₃)(Q₄₁₄), Q₄₁₁ toQ₄₁₄ have, independently from one another, the same meaning as Q₁ inclaim 1, R₄₀₁ and R₄₀₂ are each, independently from one another,hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, a C₁-C₂₀ alkyl group unsubstituted or substituted with atleast one R_(10a), a C₁-C₂₀ alkoxy group unsubstituted or substitutedwith at least one R_(10a), a C₃-C₆₀ carbocyclic group unsubstituted orsubstituted with at least one R_(10a), a C₁-C₆₀ heterocyclic groupunsubstituted or substituted with at least one R_(10a),—Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃), —N(Q₄₀₁)(Q₄₀₂), —B(Q₄₀₁)(Q₄₀₂), —C(═O)(Q₄₀₁),—S(═O)₂(Q₄₀₁), or —P(═O)(Q₄₀₁)(Q₄₀₂), Q₄₀₁ to Q₄₀₃ have, independentlyfrom one another, Q₁ in claim 1, xc11 and xc12 are each, independentlyfrom one another, an integer from 0 to 10, and * and *′ in Formula 402each is a binding site to M in Formula
 401. 4. The light-emitting deviceof claim 2, wherein the emission layer is configured to emit blue light.5. The light-emitting device of claim 2, wherein the emission layerfurther comprises a host, and an amount of the host is greater than anamount of the heterocyclic compound of Formula
 1. 6. The light-emittingdevice of claim 5, wherein the host comprises two different hostcompounds.
 7. The light-emitting device of claim 5, wherein the hostcomprises a hole transport host compound and an electron transport hostcompound.
 8. The light-emitting device of claim 1, wherein theinterlayer further comprises a hole transport region between the firstelectrode and the emission layer and an electron transport regionbetween the emission layer and the second electrode, the hole transportregion comprises a hole injection layer, a hole transport layer, anemission auxiliary layer, an electron blocking layer, or any combinationthereof, and the electron transport region comprises a buffer layer, ahole blocking layer, an electron control layer, an electron transportlayer, an electron injection layer, or any combination thereof.
 9. Thelight-emitting device of claim 8, wherein the emission layer comprisesthe heterocyclic compound of Formula 1, the hole transport regioncomprises a compound of Formula 201, a compound of Formula 202, or anycombination thereof:

wherein, in Formulae 201 and 202, L₂₀₁ to L₂₀₄ are each, independentlyfrom one another, a C₃-C₆₀ carbocyclic group unsubstituted orsubstituted with at least one R_(10a) or a C₁-C₆₀ heterocyclic groupunsubstituted or substituted with at least one R_(10a), L₂₀₅ is *—O—*′,*—S—*′, *—N(Q₂₀₁)-*′, a C₁-C₂₀ alkylene group unsubstituted orsubstituted with at least one R_(10a), a C₂-C₂₀ alkenylene groupunsubstituted or substituted with at least one R_(10a), a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least oneR_(10a), or a C₁-C₆₀ heterocyclic group unsubstituted or substitutedwith at least one R_(10a), xa1 to xa4 are each, independently from oneanother, an integer from 0 to 5, xa5 is an integer from 1 to 10, R₂₀₁ toR₂₀₄ and Q₂₀₁ are each, independently from one another, a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_(10a)or a C₁-C₆₀ heterocyclic group unsubstituted or substituted with atleast one R_(10a), R₂₀₁ and R₂₀₂ are optionally linked to each other,via a single bond, a C₁-C₅ alkylene group unsubstituted or substitutedwith at least one R_(10a), or a C₂-C₅ alkenylene group unsubstituted orsubstituted with at least one R_(10a), to form a C₈-C₆₀ polycyclic groupunsubstituted or substituted with at least one R_(10a), R₂₀₃ and R₂₀₄are optionally linked to each other, via a single bond, a C₁-C₅ alkylenegroup unsubstituted or substituted with at least one R_(10a), or a C₂-C₅alkenylene group unsubstituted or substituted with at least one R_(10a),to form a C₈-C₆₀ polycyclic group unsubstituted or substituted with atleast one R_(10a), * and *′ in L₂₀₅ each is a binding site in Formula202, na1 is an integer from 1 to
 4. 10. The light-emitting device ofclaim 9, wherein each of Formulae 201 and 202 includes at least onegroup of Formulae CY201 to CY217:

wherein, in Formulae CY201 to CY217, ring CY₂₀₁ to ring CY₂₀₄ are each,independently from one another, a C₃-C₂₀ carbocyclic group or a C₁-C₂₀heterocyclic group, at least one hydrogen in Formulae CY201 to CY217 isunsubstituted or substituted with R_(10a), and R_(10a), R_(10b), andR_(10c) are each, independently from one another: deuterium, —F, —Cl,—Br, —I, a hydroxyl group, a cyano group, or a nitro group; a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, or a C₁-C₆₀alkoxy group each, independently from one another, unsubstituted orsubstituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, a C₃-C₆₀ carbocyclic group, a C₁-C₆₀ heterocyclicgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), —P(═O)(Q₁₁)(Q₁₂), or any combination thereof; a C₃-C₆₀carbocyclic group, a C₁-C₆₀ heterocyclic group, a C₆-C₆₀ aryloxy group,or a C₆-C₆₀ arylthio group each, independently from one another,unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, aC₃-C₆₀ carbocyclic group, a C₁-C₆₀ heterocyclic group, a C₆-C₆₀ aryloxygroup, a C₆-C₆₀ arylthio group, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂),—B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), —P(═O)(Q₂₁)(Q₂₂), or anycombination thereof; or —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂),—C(═O)(Q₃₁), —S(═O)₂(Q₃₁), or —P(═O)(Q₃₁)(Q₃₂), wherein Q₁₁ to Q₁₃, Q₂₁to Q₂₃, and Q₃₁ to Q₃₃ are each, independently from one another:hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group;a nitro group; a C₁-C₆₀ alkyl group; a C₂-C₆₀ alkenyl group; a C₂-C₆₀alkynyl group; a C₁-C₆₀ alkoxy group; a C₃-C₆₀ carbocyclic group; or aC₁-C₆₀ heterocyclic group each, independently from one another,unsubstituted or substituted with deuterium, —F, a cyano group, a C₁-C₆₀alkyl group, a C₁-C₆₀ alkoxy group, a phenyl group, a biphenyl group, orany combination thereof.
 11. The light-emitting device of claim 8,wherein the emission layer comprises the heterocyclic compound ofFormula 1, the electron transport region includes a compound of Formula601:[Ar₆₀₁]_(xe11)-[(L₆₀₁)_(xe1)-R₆₀₁]_(xe21)  Formula 601 wherein, inFormula 601, Ar₆₀₁ and L₆₀₁ are each, independently from one another, aC₃-C₆₀ carbocyclic group unsubstituted or substituted with at least oneR_(10a) or a C₁-C₆₀ heterocyclic group unsubstituted or substituted withat least one R_(10a), L₆₀₁ are each, independently from one another, adivalent C₃-C₆₀ carbocyclic group unsubstituted or substituted with atleast one R_(10a) or a divalent C₁-C₆₀ heterocyclic group unsubstitutedor substituted with at least one R_(10a), xe11 is 1, 2, or 3, xe1 is 0,1, 2, 3, 4, or 5, R₆₀₁ is a C₃-C₆₀ carbocyclic group unsubstituted orsubstituted with at least one R_(10a), a C₁-C₆₀ heterocyclic groupunsubstituted or substituted with at least one R_(10a),—Si(Q₆₀₁)(Q₆₀₂)(Q₆₀₃), —C(═O)(Q₆₀₁), —S(═O)₂(Q₆₀₁), or—P(═O)(Q₆₀₁)(Q₆₀₂), xe21 is 1, 2, 3, 4, or 5, one or more of Ar₆₀₁,L₆₀₁, and R₆₀₁ are each, independently from one another, a πelectron-deficient nitrogen-containing C₁-C₆₀ cyclic group unsubstitutedor substituted with at least one R_(10a), and R_(10a) is: deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group; aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, or aC₁-C₆₀ alkoxy group each, independently from one another, unsubstitutedor substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, a C₃-C₆₀ carbocyclic group, a C₁-C₆₀heterocyclic group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), —P(═O)(Q₁₁)(Q₁₂), or any combination thereof; a C₃-C₆₀carbocyclic group, a C₁-C₆₀ heterocyclic group, a C₆-C₆₀ aryloxy group,or a C₆-C₆₀ arylthio group each, independently from one another,unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, aC₃-C₆₀ carbocyclic group, a C₁-C₆₀ heterocyclic group, a C₆-C₆₀ aryloxygroup, a C₆-C₆₀ arylthio group, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂),—B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), —P(═O)(Q₂₁)(Q₂₂), or anycombination thereof; or —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂),—C(═O)(Q₃₁), —S(═O)₂(Q₃₁), or —P(═O)(Q₃₁)(Q₃₂), wherein Q₁₁ to Q₁₃, Q₂₁to Q₂₃, Q₃₁ to Q₃₃, and Q₆₀₁ to Q₆₀₃ are each, independently from oneanother: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; acyano group; a nitro group; a C₁-C₆₀ alkyl group; a C₂-C₆₀ alkenylgroup; a C₂-C₆₀ alkynyl group; a C₁-C₆₀ alkoxy group; a C₃-C₆₀carbocyclic group or a C₁-C₆₀ heterocyclic group each, independentlyfrom one another, unsubstituted or substituted with deuterium, —F, acyano group, a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkoxy group, a phenylgroup, a biphenyl group, or any combination thereof.
 12. Thelight-emitting device of claim 11, wherein an electron transport layerin the electron transport region comprises a compound of Formula 601,and the electron transport layer further comprises a material comprisinga metal.
 13. The light-emitting device of claim 12, wherein the materialcomprises a post-transition metal complex, an alkali metal complex, analkaline earth metal complex, or any combination thereof.
 14. Thelight-emitting device of claim 1, wherein Y₁ and Y₂ are each B.
 15. Thelight-emitting device of claim 1, wherein Formula 1-2 is of Formula1-2-1 or 1-2-2:

wherein, in Formulae 1-2-1 and 1-2-2, X₁₁ to X₁₄ each have,independently from one another, the same meaning as X₁₁ to X₁₄ in claim1, X₂₁ is N or C(R₂₁), X₂₂ is N or C(R₂₂), X₂₃ is N or C(R₂₃), X₂₄ is Nor C(R₂₄), and X₂₅ is N or C(R₂₅), X₃₁ is N or C(R₃₁), X₃₂ is N orC(R₃₂), X₃₃ is N or C(R₃₃), X₃₄ is N or C(R₃₄), and X₃₅ is N or C(R₃₅),R₂₁ to R₂₅ and R₃₁ to R₃₅ each have, independently from one another, themeaning as R_(10a) in claim 1, * has the meaning as in claim 1, two ormore neighboring groups of R₂₁ to R₂₅ are optionally linked to eachother to form a C₃-C₆₀ carbocyclic group unsubstituted or substitutedwith at least one R_(10a) or a C₁-C₆₀ heterocyclic group unsubstitutedor substituted with at least one R_(10a), and two or more neighboringgroups of R₃₁ to R₃₅ are optionally linked to each other to form aC₃-C₆₀ carbocyclic group unsubstituted or substituted with at least oneR_(10a) or a C₁-C₆₀ heterocyclic group unsubstituted or substituted withat least one R_(10a).
 16. The light-emitting device of claim 1, whereinFormula 1-2 is one of Formulae 2-1 to 2-57:

wherein, in Formulae 2-1 to 2-57, V₁ to V₄ are each, independently fromone another, C or N, Z₁ to Z₅ are each, independently from one another:deuterium, —F, —Cl, —Br, —I, a cyano group, a C₁-C₂₀ alkyl group, or aC₁-C₂₀ alkoxy group; a C₁-C₂₀ alkyl group or a C₁-C₂₀ alkoxy group eachindependently from one another, substituted with deuterium, —CD₃, —CD₂H,—CDH₂, —F, —CF₃, —CF₂H, —CFH₂, —Cl, —CCl₃, —CCl₂H, —CClH₂, —Br, —CBr₃,—CBr₂H, —CBrH₂, —I, —CI₃, —CI₂H, —CIH₂, a cyano group, or anycombination thereof; a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclooctyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a C₁-C₂₀ alkylphenyl group, a naphthyl group,a fluorenyl group, a phenanthrenyl group, an anthracenyl group, athiophenyl group, a furanyl group, an indenyl group, an isoindolylgroup, an indolyl group, a carbazolyl group, a benzofuranyl group, abenzothiophenyl group, a benzosilolyl group, a dibenzofuranyl group, adibenzothiophenyl group, a dibenzosilolyl group, a benzofluorenyl group,a benzocarbazolyl group, a naphthobenzofuranyl group, anaphthobenzothiophenyl group, a naphthobenzosilolyl group, adibenzofluorenyl group, a dibenzocarbazolyl group, a dinaphthofuranylgroup, a dinaphthothiophenyl group, a dinaphthosilolyl group, anindenocarbazolyl group, an indolocarbazolyl group, abenzofuranocarbazolyl group, a benzothienocarbazolyl group, abenzosilolocarbazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolylgroup, an indazolyl group, a purinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a benzoquinoxalinyl group, a quinazolinyl group, abenzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, aphenoxazinyl group, a phenothiazinyl group, a phenoxathinyl group, abenzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, abenzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, abenzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, atetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, atriazinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group,an oxazolopyridinyl group, a thiazolopyridinyl group, abenzonaphthyridinyl group, an azafluorenyl group, anazaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranylgroup, an azadibenzothiophenyl group, an azadibenzosilolyl group, anindenopyrrolyl group, or an indolopyrrolyl group each, independentlyfrom one another, unsubstituted or substituted with deuterium, —CD₃,—CD₂H, —CDH₂, —F, —CF₃, —CF₂H, —CFH₂, —Cl, —CCl₃, —CCl₂H, —CClH₂, —Br,—CBr₃, —CBr₂H, —CBrH₂, —I, —CI₃, —CI₂H, —CIH₂, a cyano group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a cyclopentenyl group, acyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a C₁-C₂₀ alkylphenyl group, a naphthyl group,a fluorenyl group, a phenanthrenyl group, an anthracenyl group, athiophenyl group, a furanyl group, an indenyl group, an isoindolylgroup, an indolyl group, a carbazolyl group, a benzofuranyl group, abenzothiophenyl group, a benzosilolyl group, a dibenzofuranyl group, adibenzothiophenyl group, a dibenzosilolyl group, a benzofluorenyl group,a benzocarbazolyl group, a naphthobenzofuranyl group, anaphthobenzothiophenyl group, a naphthobenzosilolyl group, adibenzofluorenyl group, a dibenzocarbazolyl group, a dinaphthofuranylgroup, a dinaphthothiophenyl group, a dinaphthosilolyl group, anindenocarbazolyl group, an indolocarbazolyl group, abenzofuranocarbazolyl group, a benzothienocarbazolyl group, abenzosilolocarbazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolylgroup, an indazolyl group, a purinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a benzoquinoxalinyl group, a quinazolinyl group, abenzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, anacridinyl group, a phenanthrolinyl group, a phenazinyl group, aphenoxazinyl group, a phenothiazinyl group, a phenoxathinyl group, abenzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, abenzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, abenzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, atetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, atriazinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group,an oxazolopyridinyl group, a thiazolopyridinyl group, abenzonaphthyridinyl group, an azafluorenyl group, anazaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranylgroup, an azadibenzothiophenyl group, an azadibenzosilolyl group, anindenopyrrolyl group, an indolopyrrolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃),—N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂),or any combination thereof; or —C(Q₁)(Q₂)(Q₃), —Si(Q₁)(Q₂)(Q₃),—N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂),wherein Q₁ to Q₃ and Q₃₁ to Q₃₃ are each, independently from oneanother: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; acyano group; a nitro group; a C₁-C₆₀ alkyl group; a C₂-C₆₀ alkenylgroup; a C₂-C₆₀ alkynyl group; a C₁-C₆₀ alkoxy group; a C₃-C₆₀carbocyclic group; or a C₁-C₆₀ heterocyclic group each, independentlyfrom one another, unsubstituted or substituted with deuterium, —F, acyano group, a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkoxy group, a phenylgroup, a biphenyl group, or any combination thereof, e2 is an integerfrom 0 to 2, e3 is an integer from 0 to 3, e4 is an integer from 0 to 4,e5 is an integer from 0 to 5, e7 is an integer from 0 to 7, e11 is aninteger from 0 to 11, and * indicates a binding site to a neighboringgroup.
 17. The light-emitting device of claim 1, wherein Formula 1-1 isof Formula 1-1-1:

wherein, in Formula 1-1-1, CY₁, CY₂, X₁ to X₄, Y₁, Y₂, Ar₁ to Ar₁₀, R₁,R₂, a1, and a2 have, independently from one another, the same meaning asin claim 1, R_(3a) and R_(3b) have, independently from one another, thesame meaning as R₃ in claim 1, and R_(4a) and R_(4b) have, independentlyfrom one another, the same meaning as R₄ in claim
 1. 18. Thelight-emitting device of claim 1, wherein the light-emitting devicefurther comprises a capping layer outside the first electrode or thesecond electrode, and the capping layer comprises one or morecarbocyclic compounds, heterocyclic compounds, amine-based compounds,porphyrin derivatives, phthalocyanine derivatives, naphthalocyaninederivatives, alkali metal complexes, alkaline earth-based complexes, orany combination thereof.
 19. An electronic apparatus comprising thelight-emitting device of claim
 1. 20. The electronic apparatus of claim19, further comprising a thin-film transistor, wherein the thin-filmtransistor comprises a source electrode and a drain electrode, and thefirst electrode of the light-emitting device is electrically connectedto at least one of the source electrode and the drain electrode of thethin-film transistor.